4-Isothiocyanato-N,N-dimethyl-1-naphthalenamine → N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-thiourea

HRID 2223063Notes

Reaction equation

HRID 2223063 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:5]=2[N:4]([CH3:20])[C:3]1=[O:21].[N:22]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([N:35]([CH3:37])[CH3:36])=[CH:27][CH:26]=1)=[C:23]=[S:24]>ClC(Cl)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:5]2[N:4]([CH3:20])[C:3](=[O:21])[CH:2]([NH:1][C:23]([NH:22][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([N:35]([CH3:37])[CH3:36])=[CH:27][CH:26]=3)=[S:24])[N:8]=[C:7]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 1224654-Isothiocyanato-N,N-dimethyl-1-naphthalenamineHCID 221352663-amino-7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one2×

Product 1

HCID 10218116N-(7-chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-N'-[4-(dimethylamino)-1-naphthalenyl]-thiourea

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-amino-7-chloro-5-phenyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 1) (0.299 g, 1 mmol) in dichloroethane (15 mi) was added 4-isothiocyanato-N,N-dimethyl-1-naphthalenamine (0.230 g, 1 mmol). The reaction mixture was stirred at room temperature 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 (0.345 g, 65%). 1H-NMR (CD3OD): δ 8.25 (d, 8.4 Hz, 2H), 8.00 (d, J=8.4 Hz, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.85-7.81 (m, 2H), 7.77-7.72 (m, 2H), 7.65 (d, J=8.8 Hz, 1H), 7.61-7.58 (m, 4H), 7.51-7.47 (m, 2H), 7.29 (d, J=2.4 Hz, 1H), 6.01 (s, 1H) and 3.49 (s, 9H). MS (ESI) (M+H)+=528.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c7267343013e4713a5fa505ddda2cadb
Source dataset
uspto-grants-2008_05
Patent number
US07375101B2

Reaction notes

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