Triethylamine → HCID 22405324, compound

HRID 1956345Notes

Reaction equation

HRID 1956345 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:20]1[CH:21]=[CH:22][N:23]2[CH2:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[NH:26][CH2:25][C:24]=12.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([N:26]3[C:27]4[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=4[CH2:29][N:23]4[CH:22]=[CH:21][CH:20]=[C:24]4[CH2:25]3)=[O:16])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22405332HCID 22405332, compound

Product 1

HCID 22405324HCID 22405324, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.13 g of 4-[(4-methylphenyl)-sulfonyl]benzoyl chloride (Reference Example 42) and 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 30 ml of methylene chloride containing 7 ml of triethylamine is stirred under nitrogen atmosphere for 16 hours. The reaction mixture is diluted with ? ml of chloroform and washed with 2N HCl, water, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and columned on silica gel by elution with 7:1 to 3:1 ethyl acetate:hexane to give 1.3 g of the desired product as a solid. M+H 443.2; M+Na 465.2.

Workup

  1. additionThe reaction mixture is diluted with
  2. washof chloroform and washed with 2N HCl, water, saturated NaHCO3 and water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. washcolumned on silica gel by elution with 7:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-308c44966ddb40d4a3506d1c15d5864f
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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