Ammonia → 3,4-Dichloro-5-isothiazolecarboxylic acid amide

HRID 478133Notes

Reaction equation

HRID 478133 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](Cl)=[O:9])[S:4][N:3]=1.[NH3:11]>O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([NH2:11])=[O:9])[S:4][N:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 109768863,4-Dichloro-5-isothiazolecarbonyl chloride

Product 1

HCID 113330673,4-Dichloro-5-isothiazolecarboxylic acid amideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 0 to 10° C., 50.1 g (0.2 mol) of 3,4-dichloro-isothiazole-5-carbonyl chloride are added dropwise with stirring over a period of 30 minutes to 82 g (1.2 mol) of concentrated ammonia. After the addition, another 41 g (0.6 mol) of concentrated ammonia are added and the mixture is diluted with 70 ml of water. The mixture is allowed to warm to room temperature and stirred at this temperature for 45 minutes. The resulting precipitate is filtered off with suction, washed successive with water and petroleum ether and dried. In this manner, 32.3 g (81.8% of theory) of 3,4-dichloro-isothiazole-5-carboxamide are obtained in the form of a solid of melting point 156 to 158° C.

Workup

  1. additionAfter the addition
  2. filtrationThe resulting precipitate is filtered off with suction
  3. washwashed successive with water and petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-3a75e08db54948c8a118203cb47f7069
Source dataset
uspto-grants-2003_11
Patent number
US06642181B2

Reaction notes

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