Triethylamine → HCID 9909050, compound

HRID 2307380Notes

Reaction equation

HRID 2307380 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 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 washed sequentially with water, saturated aqueous sodium bicarbonate, 0.5 N hydrochloric acid and water. The dichloromethane solution was dried over anhydrous sodium sulfate, filtered, then evaporated in vacuo to dryness to yield an off-white foam. Purification by flash chromatography on silica gel eluting with hexane-ethyl acetate (2:1) resulted in a white foam (3.02 g), m.p. 77-80° C., MS m/z: 400 (M)+.

Workup

  1. temperaturecooled in an ice bath
  2. customThe cooling bath was removed
  3. washthe reaction mixture was washed sequentially 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 in vacuo to dryness
  7. customto yield an off-white foam
  8. customPurification by flash chromatography on silica gel eluting with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2edf90ff2ef74439aa53b01fa601bfb2
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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