Thionyl Chloride → 4-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide

HRID 339528Notes

Reaction equation

HRID 339528 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]3[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=3[N:33]=2)=[CH:25][CH:24]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:16][C:2]([F:1])([F:17])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[S:30][C:31]4[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=4[N:33]=3)=[CH:27][CH:28]=2)=[O:13])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 223614014-(4,4,4-Trifluorobutoxy)benzoic acid

Product 1

HCID 673125284-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideYield 87.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-(4,4,4-trifluorobutoxy)benzoic acid (0.20 g, 0.806 mmol) and thionyl chloride (0.42 g, 3.54 mmol) in chloroform (5 ml) was heated under reflux for 8 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 (0.206 g, 0.806 mmol) in dry pyridine (10 ml) to give the title compound (0.343 g, 87%) as a colourless solid after work-up.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 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-d06e25573834415e9dabda2a1e5b6968
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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