Triethylamine → HCID 21476237, compound

HRID 2293288Notes

Reaction equation

HRID 2293288 reaction equation
[CH:1]1[C:10]2[C:9]3[CH2:11][CH2:12][CH:13]=[CH:14][C:8]=3[N:7]=[CH:6][CH2:5][C:4]=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(CC)CC)C>C(Cl)Cl>[CH:1]1[C:10]2[C:9]3[CH2:11][CH:12]([C:25]([C:24]4[CH:23]=[CH:22][C:21]([NH:20][C:18](=[O:19])[C:17]5[CH:30]=[CH:31][CH:32]=[CH:33][C:16]=5[CH3:15])=[CH:29][CH:28]=4)=[O:26])[CH:13]=[CH:14][C:8]=3[N:7]=[CH:6][CH2:5][C:4]=2[S:3][CH:2]=1

Participants

5

Reactant 3

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

Product 1

HCID 21476237HCID 21476237, compoundYield 59.4%

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-64c3e8045bf441c397c3dc4a8de856ff
Source dataset
uspto-grants-1997_11
Patent number
US05686445

Reaction notes

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