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Triethylamine → N-[4-[(5,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepin-4-yl)carbonyl]phenyl]-3,4-dichlorobenzamide

HRID 2255981
Notes
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Reaction equation

HRID 2255981 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]3[S:15][CH:16]=[CH:17][C:9]2=3)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[Cl:37])[C:31](Cl)=[O:32]>ClCCl>[S:15]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][N:8]([C:6]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:31](=[O:32])[C:30]4[CH:34]=[CH:35][C:36]([Cl:37])=[C:28]([Cl:27])[CH:29]=4)=[CH:19][CH:18]=3)=[O:7])[C:9]=2[CH:17]=[CH:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 214671424-(4-Aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

Product 1

HCID 21467135N-[4-[(5,6,7,8-Tetrahydro-4H-thieno[3,2-b]azepin-4-yl)carbonyl]phenyl]-3,4-dichlorobenzamideYield 51.8%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 0.30 g of 4-(4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine and 0.208 ml of triethylamine in 10 ml of dichloromethane is added, under argon, 0.251 g of 3,4-dichlorobenzoyl chloride. The mixture is stirred overnight and concentrated to dryness under vacuum. The residue is dissolved in ethyl acetate and the solution washed with H2O, 2N citric acid, NaHCO3 solution, brine and dried (Na2SO4). The solvent is removed and the residual yellow solid crystallized from ethyl acetate-hexane to give 0.254 g of crystals, m.p. 154°-160° C.

Workup

  1. concentrationconcentrated to dryness under vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washthe solution washed with H2O, 2N citric acid, NaHCO3 solution, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed
  6. customthe residual yellow solid crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-55ed7d671c554698b4effd3616d7a7f7
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05654297

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes