Ethyl thiooxamate → Ethyl 4,5-bis(4-methoxyphenyl)thiazole-2-carboxylate

HRID 1587399Notes

Reaction equation

HRID 1587399 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)Cl)=[CH:5][CH:4]=1.[NH2:21][C:22](=[S:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:21]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:28][C:10]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-one

Product 1

HCID 10429180Ethyl 4,5-bis(4-methoxyphenyl)thiazole-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (5.00 g) and ethyl 2-amino-2-thioxoacetate (3.44 g) in ethanol (30 ml) was refluxed for 4 hours. After allowing to cool to ambient temperature, the reaction mixture was filtered and washed with ethanol, and the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel (300 g) and eluted with a mixture of hexane and ethyl acetate (8:1, V/V). The fractions containing the object compound were combined and concentrated under reduced pressure, and to give a oily compound of 4,5-bis(4-methoxyphenyl)-2-ethoxycarbonylthiazole (6.10 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. filtrationthe reaction mixture was filtered
  3. washwashed with ethanol
  4. customthe filtrate was evaporated in vacuo
  5. washeluted with a mixture of hexane and ethyl acetate (8:1, V/V)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bf0920aec9b4d2dae712580e8258fc6
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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