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4-Fluorobenzoyl chloride → N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide

HRID 1582142
Notes
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Reaction equation

HRID 1582142 reaction equation
[CH:1]1([C:7]2[C:15]3[S:14][C:13]([NH2:16])=[N:12][C:11]=3[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>C1COCC1>[CH:1]1([C:7]2[C:15]3[S:14][C:13]([NH:16][C:33](=[O:34])[C:32]4[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=4)=[N:12][C:11]=3[C:10]([O:17][CH3:18])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 227195747-Cyclohexyl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 9952034N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamideYield 14%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.05 g (0.19 mMol) 7-cyclohexyl-4-methoxy-benzothiazol-2-ylamine in 2 ml THF were added 0.1 ml ethyl diisopropyl amine and 0.027 ml (0.23 mMol) 4-fluoro-benzoyl chloride. The reaction mixture was heated to 70° C. for 2 h. The solvent was evaporated to dryness, the residue taken up in dichloro methane and washed with water and brine. The organic phase was dried over sodium sulfate and evaporated to dryness in vacuo. The residue was subjected to column chromatography (ethyl acetate/hexane 1:9, 1:4) to yield 0.01 g (14%) of N-(7-cyclohexyl-4-methoxy-benzothiazol-2-yl)-4-fluoro-benzamide as a light yellow solid; F.p.: 192-195° C.

Workup

  1. customThe solvent was evaporated to dryness
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-d6d6fc2e4af94ca5b8ce9d321944528c
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06734179B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes