Triethylamine → HCID 9909050, compound

HRID 378893Notes

Reaction equation

HRID 378893 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.[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([Cl:32])[CH:24]=1>ClCCl>[Br:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:28])=[C:25]([Cl:32])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 155922074-Bromo-2-chlorobenzoyl chloride

Product 1

HCID 9909050HCID 9909050, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 10,11-dihydro-5H-pyrrolo [2,1-c][1,4] benzodiazepine (1.44 g) and triethylamine (0.95 g) in dichloromethane (40 mL) cooled in an ice bath, was added dropwise a solution of the crude 4-bromo-2-chlorobenzoyl chloride (2.42 g) in dichloromethane (20 mL). The cooling bath was removed and after stirring for 22 hours, the reaction mixture was sequentially washed with water, saturated aqueous sodium bicarbonate, 0.5 N hydrochloric acid and water. The dichloromethane solution was dried over anhydrous sodium sulfate, filtered and then evaporated to dryness to yield an off-white foam. Purification by flash chromatography on silica gel Merck-60 eluting with hexane-ethyl acetate (2:1) resulted in a white solid (3.02 g), m.p. 77-80° C.

Workup

  1. temperaturecooled in an ice bath
  2. customThe cooling bath was removed
  3. washthe reaction mixture was sequentially washed with water, saturated aqueous sodium bicarbonate, 0.5 N hydrochloric acid and water
  4. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield an off-white foam
  8. customPurification by flash chromatography on silica gel
  9. washeluting with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-00347adcbaee4f389121517752a08ac3
Source dataset
uspto-grants-2001_10
Patent number
US06297234B1

Reaction notes

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