5-AMINO-DI-T-BUTYL ISOPHTHALATE synthesis
- Product Name:5-AMINO-DI-T-BUTYL ISOPHTHALATE
- CAS Number:167993-12-6
- Molecular formula:C16H23NO4
- Molecular Weight:293.36
99-31-0
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Yield:167993-12-6 15%
Reaction Conditions:
in chloroform;
Steps:
Di-t-butyl 5-aminoisophthalate (7.59) (Figure 7.17)
Di-t-butyl 5-aminoisophthalate (7.59) (Figure 7.17) The procedure used was a low pressure modification of the method outlined by McCloskey (Ref. 213) for esterifying hindered acids. A stirred suspension of 5-aminoisophthalic acid (7.39) (6.48 g, 33.6 mmol) in CHCl3(100 ml) was cooled to -10°C. The reaction mixture was then saturated with isobutylene gas and conc. sulfuric acid (2.5 ml) was added dropwise. The reaction vessel was stoppered and the reaction mixture was allowed to warm to room temperature. After 4 d the reaction was quenched by pouring onto a mixture of crushed ice and solid NaHCO3. The organic layer was washed with water (3 x 200 ml), brine (2 x 100 ml), and dried (MgSO4). After filtration, the solvent and volatiles were removed under reduced pressure to yield the title compound 7.59 as a pale pink solid (1.48 g, 15%). δH (250 Mhz, d6-DMSO) 1.60 (18H, s, CH3). 5.47 (2H, s, NH), 7.38 (2H, s, 2 Ar-H), 7.65 (1H, s, Ar-H).
References:
EP745673,1996,A2
618-88-2
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