Phosphorus oxychloride → Ethyl 2-(2-amino-1,3-thiazol-4-yl)glyoxylate hydrochloride

HRID 325383Notes

Reaction equation

HRID 325383 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1)=O.P(Cl)(Cl)([Cl:18])=O>C(O)C>[ClH:18].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 2733245Ethyl 2-(formylamino)-alpha-oxo-4-thiazoleacetateHCID 178473042HCID 178473042, compound

Product 1

HCID 20254350Ethyl 2-(2-amino-1,3-thiazol-4-yl)glyoxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 2-(2-formylamino-1,3-thiazol-4-yl)glyoxylate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate, (31.3 g.) in ethanol (600 ml.) was dropwise added phosphorus oxychloride (41.9 g.) under ice-cooling and stirring, and the mixture was stirred for 30 minutes at 50° C. After the reaction, the solvent was distilled off. The residue was washed with diethyl ether and then dried to give ethyl 2-(2-amino-1,3-thiazol-4-yl)glyoxylate hydrochloride, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)glyoxylate hydrochloride, in quantitative yield, mp. 263° to 264° C. (dec.).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes at 50° C
  3. customAfter the reaction
  4. distillationthe solvent was distilled off
  5. washThe residue was washed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-081c946e0e194ab1ac22dcfaf58d2296
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Reaction notes

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