Thionyl Chloride → HCID 67240460, compound

HRID 339522

Reaction equation

HRID 339522 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.S(Cl)(Cl)=O.COC1C(C(F)(F)F)=CC(C(Cl)=O)=CC=1.[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[S:43][C:44]3[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:45]=3[N:46]=2)=[CH:38][CH:37]=1>N1C=CC=CC=1>[F:13][C:12]([F:15])([F:14])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[S:43][C:44]3[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:45]=3[N:46]=2)=[CH:40][CH:41]=1)=[O:9]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 27752944-methoxy-2-(trifluoromethyl)benzoic AcidHCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chloride

Product 1

HCID 67240460HCID 67240460, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A stirred mixture of 4-methoxy-2-trifluoromethylbenzoic acid (0.50 g, 2.27 mmol) and thionyl chloride (9 ml) was heated under reflux for 4 h. After cooling to room temperature, the excess reagent was removed under reduced pressure to give crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude 4-methoxy-5-trifluoromethylbenzoyl chloride and 2-(4-aminophenyl)-6-methoxybenzo thiazole (0.58 g, 2.27 mmol) in dry pyridine (15 ml) to give the title compound (0.478 g, 46%) as pale yellow needles after work-up and recrystallisation from acetic acid.

Workup

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

Sources & evidence

ORD record
ord-d3daccfe68cc4410bdbac4b9d5eab2e2
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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