Dimethylformamide → 4,5-Diphenyl-2-oxazolyl mercaptoacetic acid

HRID 2072542

Reaction equation

HRID 2072542 reaction equation
C[O-].[Na+].CN(C=O)C.Cl.C(N(CC)CCCl)C.[Na+].[C:19]1([C:25]2[N:26]=[C:27]([CH:36]([SH:40])[C:37]([O-:39])=[O:38])[O:28][C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.Cl>[C:19]1([C:25]2[N:26]=[C:27]([CH:36]([SH:40])[C:37]([OH:39])=[O:38])[O:28][C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 10942334Sodium MethoxideHCID 1317109224,5-Diphenyl-2-oxazolyl-mercaptoacetic acid sodium salt

Product 1

HCID 214083604,5-Diphenyl-2-oxazolyl mercaptoacetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

3 g. of sodium methylate is suspended in 100 ml. of DMF, 9.5 g. of 2-diethylaminoethyl chloride hydrochloride is added thereto, and the reaction mixture is stirred for 20 minutes at room temperature. Then, 16.7 g. of 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid sodium salt is added. Under agitation, the reaction mixture is heated to 80° for 40 hours, then diluted with water, dilute hydrochloric acid is added to a pH of 2-3, and the reaction solution is washed with ethyl acetate. Then, the pH of the aqueous solution is adjusted to 9. The mixture is worked up as usual, thus obtaining the 2-diethylaminoethyl ester of 4,5-diphenyl-2-oxazolyl-mercaptoacetic acid; hydrochloride, m.p. 160°-162°.

Workup

  1. temperatureUnder agitation, the reaction mixture is heated to 80° for 40 hours
  2. additionis added to a pH of 2-3
  3. washthe reaction solution is washed with ethyl acetate

Sources & evidence

ORD record
ord-b188b93fb3c74c35bf844695c940f825
Source dataset
uspto-grants-1977_09
Patent number
US04051250

Linked notes

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