Thioglycolic Acid → HCID 57054872, compound

4-Amino-3,5-dichlorobenzoic acid ethyl ester (17.7 g) was dissolved in a mixture of acetic acid (75 mL) and dichloromethane (75 mL) and then methanesulfonic acid (22 mL) was added. 3-Methylbutyl nitrite (10 mL) was added to the solution while the temperature was kept at 0-5° C. After 30 min, mercaptoacetic acid (38 mL) was added at 0-5° C. Then a part of the dichloromethane was removed by distillation which was stopped when the internal temperature of the mixture was 80° C. and this temperature was kept for additional 45 min. The mixture was cooled and the rest of the solvents were evaporated under vacuum. Toluene (300 mL), water (200 mL) and hydrochloric acid (6 M, 80 mL) were added. The organic phase was separated and then extracted with potassium bicarbonate solution (1 M, 200 mL) which was acidified with hydrochloric acid (6M, 50 mL). The product was extracted to toluene (100 mL) which was dried (sodium sulphate) and evaporated to dryness (yield 5.1 g). 1H-NMR (400 MHz, DMSO-d6) d=1.33 (t, J=7.0 Hz, 3H), 3.74 (s, 2H), 4.34 (q, J=7.0 Hz, 2H), 7.97 (s, 2H), 12.5 (b, 1H).

1. customwas kept at 0-5° C
2. customThen a part of the dichloromethane was removed by distillation which
3. customwas 80° C.
4. waitthis temperature was kept for additional 45 min
5. temperatureThe mixture was cooled
6. customthe rest of the solvents were evaporated under vacuum
7. additionToluene (300 mL), water (200 mL) and hydrochloric acid (6 M, 80 mL) were added
8. customThe organic phase was separated
9. extractionextracted with potassium bicarbonate solution (1 M, 200 mL) which
10. extractionThe product was extracted to toluene (100 mL) which
11. dry with materialwas dried (sodium sulphate)
12. customevaporated to dryness (yield 5.1 g)

ORD record

ord-f52eac46c8af426bad8a7fb4c7b20ec1

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06201027B1