Acetic Anhydride → Methyl 5-formamido-1,2,4-thiadiazole-3-carboxylate

HRID 543828Notes

Reaction equation

HRID 543828 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[S:13][N:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[N:10]=1>C(O)=O>[CH:1]([NH:8][C:9]1[S:13][N:12]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[N:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13577102Methyl 5-amino-1,2,4-thiadiazole-3-carboxylate

Product 1

HCID 13577103Methyl 5-formamido-1,2,4-thiadiazole-3-carboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a mixture of formic acid (33 g) and acetic anhydride (22 g) was added methyl 5-amino-1,2,4-thiadiazole-3-carboxylate (6.2 g), and then the mixture was stirred for 2 days at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was triturated with a mixture of diethyl ether and n-hexane to give the title compound (7.2 g), mp. 210° to 215° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-6d2d9cbc2518435e88b46f6ddfc961a9
Source dataset
uspto-grants-1984_05
Patent number
US04447429

Reaction notes

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