Triethylamine → HCID 15308000, compound

HRID 1598766Notes

Reaction equation

HRID 1598766 reaction equation
[CH:1]1[C:10]2[C:9]3C[CH2:12][CH:13]=[CH:14][C:8]=3N=CCC=2[S: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:36]([CH2:39][CH3:40])[CH2:37][CH3:38])C>C(Cl)Cl>[S:3]1[C:40]2[CH2:39][N:36]([C:25]([C:24]3[CH:28]=[CH:29][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:22][CH:23]=3)=[O:26])[C:37]3[CH:38]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:9][C:10]=2[CH:1]=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl ChlorideHCID 18929554HCID 18929554, compound

Product 1

HCID 15308000HCID 15308000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 400 mg of 9,10-dihydro-4H-thieno[2,3-d][1]benzazepine and 600 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 water and chloroform. The organic layer is dried (Na2 SO4) 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 518 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 water and chloroform
  4. customThe organic layer is dried (Na2 SO4)
  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-8b7a917a0cce4698a144382c6670c6e8
Source dataset
uspto-grants-1998_04
Patent number
US05739128

Reaction notes

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