Hydrochloric Acid → HCID 22717664, compound

HRID 1582541Notes

Reaction equation

HRID 1582541 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Cl:11])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].Cl>N1C=CC=CC=1>[Cl:11][C:4]1[S:3][C:2]([NH:1][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([Cl:12])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=2)=[N:6][C:5]=1[C:7]([F:10])([F:8])[F:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 1781935-Chloro-4-(trifluoromethyl)-1,3-thiazol-2-amine

Product 1

HCID 22717664HCID 22717664, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-5-chloro-4-trifluoromethylthiazole (1.0 g) was dissolved in pyridine (5 ml) and 4-chloro-3-nitrobenzoylchloride (1.1 g) was added at room temperature with stirring. The mixture was stirred for 1 day at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The chloroform layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The solid thus obtained was recrystallized from methanol to give N-(5-chloro-4-trifluoromethylthiazol-2-yl)-4-chloro-3-nitro-benzamide (0.83 g), m. p. 183-184° C.

Workup

  1. stirringThe mixture was stirred for 1 day at room temperature
  2. extractionthen extracted with chloroform
  3. dry with materialThe chloroform layer was dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe solid thus obtained
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-27146999a9c6476d9c2e1b2691c75e24
Source dataset
uspto-grants-2004_05
Patent number
US06737382B1

Reaction notes

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