Hydrochloric Acid → HCID 11704456, compound

HRID 1582540Notes

Reaction equation

HRID 1582540 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:11])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:16](Cl)=[O:17].Cl>N1C=CC=CC=1>[Br:11][C:4]1[S:3][C:2]([NH:1][C:16](=[O:17])[C:15]2[CH:19]=[CH:20][C:21]([Cl:22])=[C:13]([Cl:12])[CH:14]=2)=[N:6][C:5]=1[C:7]([F:10])([F:8])[F:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 157107015-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine

Product 1

HCID 11704456HCID 11704456, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-5-bromo-4-trifluoromethylthiazole (1.0 g) was dissolved in pyridine (5 ml) and 3,4-dichlorobenzoylchloride (0.85 g) was added at room temperature with stirring. The mixture was stirred for 5 hr 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-bromo-4-trifluoromethylthiazol-2-yl)-3,4-dicloro-benzamide (1.29 g), m. p. 191-192° C.

Workup

  1. stirringThe mixture was stirred for 5 hr 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-a476a5b1f0824b07b9dd2ee20708fcfb
Source dataset
uspto-grants-2004_05
Patent number
US06737382B1

Reaction notes

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