N,N-dimethyl-p-phenylenediamine → HCID 10288797, compound

HRID 2223060Notes

Reaction equation

HRID 2223060 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([N:14]=[C:15]=[S:16])[N:8]=[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:6]=2[CH:23]=1.[CH3:24][N:25]([CH3:33])[C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([NH:14][C:15]([NH:32][C:29]3[CH:30]=[CH:31][C:26]([N:25]([CH3:33])[CH3:24])=[CH:27][CH:28]=3)=[S:16])[N:8]=[C:7]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:23]=1

Participants

4

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 86600074HCID 86600074, compound2×

Product 1

HCID 10288797HCID 10288797, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-chloro-1,3-dihydro-3-isothiocyanato-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 7) (0.342 g, 1 mmol) in dichloromethane (20 ml) was added N,N-dimethyl-1,4-benzenediamine (0.136 g, 1 mmol). The reaction mixture was heated at reflux for 17 hours. The solvent was evaporated in vacuo, the residue was triturated with ether and the title compound was obtained as a colorless solid (0.167 g, 35%). 1H-NMR (CDCl3): δ 7.70-7.22 (m, 10H), 6.75 (d, J=8.8 Hz, 2H), 6.05 (d, J=7.6 Hz, 1H), 3.42 (s, 3H) and 2.98 (s, 6H). MS (ESI) (M+H)+=478.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-4233fb435fc14550af5449beda2aa801
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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