Triethylamine → HCID 22405321, compound

HRID 440778Notes

Reaction equation

HRID 440778 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(CC)CC)C.[C:22]1([S:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:22]1([S:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:34])=[CH:31][CH:30]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 20444606HCID 20444606, compound

Product 1

HCID 22405321HCID 22405321, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.0 g of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 50 ml of dry methylene chloride, under nitrogen, and cooled to 0° C. is added 5.0 ml of triethylamine followed by a solution of 2.16 g of 4-(phenylthio)benzoyl chloride (Reference Example 34) in 30 ml of methylene chloride. The reaction mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with 50 ml of chloroform and washed with 50 ml each of water, 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 1.92 g of the desired product as a solid. M+H 397.1 M+Na 419.1.

Workup

  1. washwashed with 50 ml each of water, 2N HCl, water, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. washcolumned on silica gel by elution with 7:1 to 3:1 ethyl acetate

Sources & evidence

ORD record
ord-c1bbcd3886a44e4880f9651ee507a83a
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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