Potassium Hydroxide → HCID 86735743, compound

HRID 839044Notes

Reaction equation

HRID 839044 reaction equation
[OH-].[K+:2].[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]([OH:11])=[O:10].S1C=CC=C1[CH2:17][C:18]([O-])=[O:19].[K+].[CH3:22][O:23][C:24](=[O:40])[CH2:25][NH:26][C:27](=[O:39])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=O)[CH2:36]Cl)[CH:29]=1>CO>[S:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][C:9]([O-:11])=[O:10].[K+:2].[CH3:22][O:23][C:24](=[O:40])[CH2:25][NH:26][C:27](=[O:39])[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][C:35](=[S:3])[CH2:36][C:18](=[O:19])[CH3:17])[CH:29]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 159702-Thiopheneacetic acidHCID 23696799Potassium 2-thienylacetateHCID 54361407HCID 54361407, compound

Product 2

HCID 23696799Potassium 2-thienylacetateHCID 86735743HCID 86735743, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of potassium thiolacetate is prepared by adding 495 ml. of 2N-methanolic potassium hydroxide (0.99 mole) during a period of 15 min. to a solution of 74.3 ml. of thiolacetic acid (79.1 g., 1.04 mole) and 500 ml. of methanol while maintaining a temperature of 1°-5° C. The methanolic potassium thiolacetate solution thus prepared is added over 0.5 hr. to a mixture of N-[3-(chloroacetylamino)benzoyl]glycine methyl ester (267.5 g., 0.94 mole) in 2 l. of methanol while maintaining a temperature of 0°-5° C. After stirring for a period of 1 hr. without cooling, the reaction mixture is warmed at 40°-45° C. for 2 hrs., cooled, and filtered. The material collected is sequentially washed with 50% methanol, water, and 50% methanol, and then air dried to afford 262.4 g. (86% yield) of N-[3-(acetylthioacetylamino)benzoyl]glycine methyl ester, m.p. 86°-88° C. Crystallization from methanol provides analytically pure N-[3-(acetylthioacetylamino)benzoyl]glycine methyl ester, m.p. 90.0°-92.0° C.

Workup

  1. additionby adding 495 ml
  2. additionis added over 0.5 hr
  3. temperaturewithout cooling
  4. temperaturethe reaction mixture is warmed at 40°-45° C. for 2 hrs
  5. temperature, cooled
  6. filtrationfiltered
  7. customThe material collected
  8. washis sequentially washed with 50% methanol, water, and 50% methanol
  9. customair dried
  10. customto afford 262.4 g

Sources & evidence

ORD record
ord-5860766d1f3444e7ac10ec77c7d59a8e
Source dataset
uspto-grants-1978_06
Patent number
US04093739

Reaction notes

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