Thionyl Chloride → 4-(3,3,3-Trifluoropropoxy)-n-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide

HRID 339527Notes

Reaction equation

HRID 339527 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=1.S(Cl)(Cl)=O.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:29][C:30]3[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:31]=3[N:32]=2)=[CH:24][CH:23]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:15][C:2]([F:1])([F:16])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[S:29][C:30]4[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:31]=4[N:32]=3)=[CH:26][CH:27]=2)=[O:12])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 581116554-(3,3,3-Trifluoropropoxy)benzoic acid

Product 1

HCID 672387034-(3,3,3-Trifluoropropoxy)-n-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-(3,3,3-trifluoropropoxy)benzoic acid (0.32 g, 1.39 mmol) and thionyl chloride (0.33 g, 2.78 mmol) in chloroform (5 ml) was heated under reflux for 5 h. The reaction mixture was cooled to room temperature and the excess reagent and solvent was removed under reduced pressure to give the crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude acid chloride and 2-(4-aminophenyl)-6-methoxybenzothiazole (0.36 g, 1.39 mmol) in dry pyridine (10 ml) to give the title compound (0.59 g, 90%) as a pale yellow solid after work-up.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. customthe excess reagent and solvent was removed under reduced pressure
  4. customto give the crude acid chloride
  5. customThe amide was prepared

Sources & evidence

ORD record
ord-60bbe50994d8469399a42abdcc8598f1
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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