Hydrochloric Acid → Acetic acid, oxo((4-phenyl-2-thiazolyl)amino)-, 2-methoxyethyl ester

HRID 647122Notes

Reaction equation

HRID 647122 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13](=[O:17])[C:14]([OH:16])=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O-:21])(=O)[CH3:19].[K+].Cl.[C:24](Cl)(=O)C(Cl)=O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13](=[O:17])[C:14]([O:16][CH2:19][CH2:18][O:21][CH3:24])=[O:15])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 517044Potassium AcetateHCID 4713520N-(4-phenyl-thiazol-2-yl)-oxamic acid

Product 1

HCID 3067448Acetic acid, oxo((4-phenyl-2-thiazolyl)amino)-, 2-methoxyethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.2 g of N-(4-phenyl-thiazol-2-yl)-oxamic acid (prepared from the ethyl ester by hydrolyzing with aqueous potassium acetate and liberating the acid with dilute hydrochloric acid), in 25 ml of dry toluene, are heated with 20 ml of oxalyl chloride for 2 hours at 60° C. After distilling off the excess oxalyl chloride under reduced pressure, a solution of 5 ml of ethylene glycol monomethyl ether, 3.5 ml of triethylamine and 20 ml of toluene is added dropwise. The mixture is stirred for a further 3 hours at room temperature and is then left to stand overnight. The precipitate is filtered off, washed with methanol and water and recrystallized from ethanol. 3.7 g of the compound of the formula I, with R1 =C6H5 and R2 =CH2CH2OCH3, of melting point 118°-120° C., are obtained.

Workup

  1. distillationAfter distilling off the excess oxalyl chloride under reduced pressure
  2. additiona solution of 5 ml of ethylene glycol monomethyl ether, 3.5 ml of triethylamine and 20 ml of toluene is added dropwise
  3. waitis then left
  4. waitto stand overnight
  5. filtrationThe precipitate is filtered off
  6. washwashed with methanol and water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f8d2c993b5244a7a85cf80b523e41f0f
Source dataset
uspto-grants-1983_10
Patent number
US04407810

Reaction notes

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