Thionyl Chloride → 4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzonitrile

HRID 558946Notes

Reaction equation

HRID 558946 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[CH3:12])#[N:2].S(Cl)(Cl)=O.[CH:17]1[CH:18]=[CH:19][N:20]2[CH2:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[NH:23][CH2:22][C:21]=12>C1(C)C=CC=CC=1>[CH:17]1[CH:18]=[CH:19][N:20]2[CH2:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]([C:7]([C:6]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[C:4]([CH3:12])[CH:5]=3)=[O:9])[CH2:22][C:21]=12

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 102410994-Cyano-3-methylbenzoic acidHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 251783794-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-cyano-3-methylbenzoic acid from Example C (1.2 g, 7.5 mmol) and thionyl chloride (3.6 ml, 54 mmol) in toluene (20 ml) was heated at reflux for 2 h. The mixture was evaporated and azeotroped with toluene. The residue was dissolved in dichloromethane, 10,11-dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine (1.4 g, 7.5 mmol) was added and the mixture stirred for 18 h. The mixture was evaporated and the residue purified by flash chromatography on silica (EtOAc:pet ether, 30:70 to 80:20) to give a cream solid, yield 1.5 g, 63%.

Workup

  1. temperatureat reflux for 2 h
  2. customThe mixture was evaporated
  3. customazeotroped with toluene
  4. dissolutionThe residue was dissolved in dichloromethane
  5. customThe mixture was evaporated
  6. customthe residue purified by flash chromatography on silica (EtOAc:pet ether, 30:70 to 80:20)
  7. customto give a cream solid, yield 1.5 g, 63%

Sources & evidence

ORD record
ord-7c0ceed90a42411ab09df0b3a068f13a
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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