Triethylamine → HCID 15307998, compound

HRID 355940Notes

Reaction equation

HRID 355940 reaction equation
[S:1]1[C:10]2[CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[NH:6][CH2:5][C:4]=2[CH:3]=[CH:2]1.[CH3:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:19].C(N(CC)CC)C>C(Cl)Cl>[S:1]1[C:10]2[CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[N:6]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:18](=[O:19])[C:17]4[CH:30]=[CH:31][CH:32]=[CH:33][C:16]=4[CH3:15])=[CH:29][CH:28]=3)=[O:26])[CH2:5][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 108673664,10-Dihydro-5H-thieno[3,2-c][1]benzazepine

Product 1

HCID 15307998HCID 15307998, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 400 mg of 4,10-dihydro-5H-thieno[3,2-c][1]benzazepine and 700 mg of 4-[(2-methylbenzoyl)amino]benzoyl chloride is stirred in 30 ml of methylene chloride in the presence of 3 ml of triethylamine for 8 hours. The volatiles are removed in vacuo to give a residue which is partitioned between chloroform and water. The organic layer is dried (Na2SO4) and the filtrate evaporated in vacuo to give a residue which is purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane to give 543 mg of the desired product. M+1=439.

Workup

  1. customThe volatiles are removed in vacuo
  2. customto give a residue which
  3. customis partitioned between chloroform and water
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe filtrate evaporated in vacuo
  6. customto give a residue which
  7. customis purified by column chromatography on silica gel by elution with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-182466c45ccc4e1a84b01775de85173b
Source dataset
uspto-grants-1998_11
Patent number
US05834461

Reaction notes

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