Hydrochloric Acid → N-(5-bromo-4-methylthiazol-2-yl)-2,6-difluorobenzamide

HRID 1255115Notes

Reaction equation

HRID 1255115 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:11])=[C:5]([C:7](F)(F)F)[N:6]=1.[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:14]=1[C:15](Cl)=[O:16].Cl>C1COCC1.N1C=CC=CC=1>[Br:11][C:4]1[S:3][C:2]([NH:1][C:15](=[O:16])[C:14]2[C:13]([F:12])=[CH:21][CH:20]=[CH:19][C:18]=2[F:22])=[N:6][C:5]=1[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 874382,6-Difluorobenzoyl chlorideHCID 157107015-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine

Product 1

HCID 59004504N-(5-bromo-4-methylthiazol-2-yl)-2,6-difluorobenzamideYield 83%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-bromo-4-trifluoromethylthiazole (0.8 g) was dissolved in 3 mL of 1:1 mixture of THF and pyridine. 2,6-difluorobenzoylchloride (0.6 g) was added at room temperature with stirring. The mixture was stirred for 3 hours at room temperature. The mixture was poured into ice water and acidified with aqueous hydrochloric acid then extracted with chloroform. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography on silica gel gave the title compound as a white solid. Yield 83%.

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. extractionthen extracted with chloroform
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4b25ee29242644d2a6e5c548bebbf70c
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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