Ammonia → Methyl 5-sulfamoyl-1,3-thiazole-4-carboxylate

HRID 2073697Notes

Reaction equation

HRID 2073697 reaction equation
Cl[S:2]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3].[NH3:14]>O1CCCC1>[NH2:14][S:2]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15077125Methyl 5-(chlorosulfonyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 15077126Methyl 5-sulfamoyl-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 28.9 g of methyl 5-(chlorosulfonyl)-4-thiazolecarboxylate in 150 ml tetrahydrofuran was cooled to 0° and 6.6 ml of liquid ammonia was added dropwise at 0°-10°. The suspension was allowed to warm to ambient temperature and stirred 1 hour. The reaction mixture was filtered, the ammonium chloride washed with tetrahydrofuran, and the solvent evaporated from the filtrate. The residual solid was slurried in hexane, collected and dried to give 25.0 g of the title compound, m.p. 138°-140°. IR: 3.01 and 3.1μ (SO2NH2) and 5.8μ (C=O).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe ammonium chloride washed with tetrahydrofuran
  3. customthe solvent evaporated from the filtrate
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-288027ee87514240a048d654d6e10fec
Source dataset
uspto-grants-1990_04
Patent number
US04919706

Reaction notes

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