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

HRID 339534Notes

Reaction equation

HRID 339534 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[S:26][C:27]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]=3[N:29]=2)=[CH:21][CH:20]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[S:26][C:27]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]=4[N:29]=3)=[CH:23][CH:24]=2)=[O:11])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 513570934-(2-Fluoroethoxy)benzoic acid

Product 1

HCID 873520044-(2-Fluoroethoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideYield 72.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-(2-fluoroethoxy)benzoic acid (0.20 g, 1.11 mmol) and thionyl chloride (0.53 g, 4.44 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 (0.28 g, 1.11 mmol) in dry pyridine (10 ml) to give the title compound (0.34 g, 72%) 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-fafbb656e0124645ac928c5a93940e39
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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