Hydrochloric Acid → HCID 22717663, compound

HRID 1582542Notes

Reaction equation

HRID 1582542 reaction equation
[NH2:1][C:2]1[S:3][C:4]([I:11])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[F:12][C:13]([F:28])([F:27])[C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1)[C:17](Cl)=[O:18].Cl>N1C=CC=CC=1>[I:11][C:4]1[S:3][C:2]([NH:1][C:17](=[O:18])[C:16]2[CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=[C:14]([C:13]([F:12])([F:27])[F:28])[CH:15]=2)=[N:6][C:5]=1[C:7]([F:10])([F:8])[F:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 227176715-Iodo-4-(trifluoromethyl)-1,3-thiazol-2-amine

Product 1

HCID 22717663HCID 22717663, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Amino-5-iodo-4-trifluoromethylthiazole (1.0 g) was dissolved in pyridine (2 ml) and 3,5-bis-trifluoromethylbenzoylchloride (0.95 g) was added at room temperature with stirring. The mixture was stirred for 6 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-iodo-4-trifluoromethylthiazol-2-yl)-3,5-bis-trifluoromethylbenzamide (1.3 g), m. p. 172-173° C.

Workup

  1. stirringThe mixture was stirred for 6 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-415e641e0a1143ae9382700f88385343
Source dataset
uspto-grants-2004_05
Patent number
US06737382B1

Reaction notes

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