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

HRID 2223061Notes

Reaction equation

[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:6]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:5]=2[N:4]([CH3:21])[C:3]1=[O:22].[N:23]([C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([N:36]([CH3:38])[CH3:37])=[CH:28][CH:27]=1)=[C:24]=[S:25]>ClC(Cl)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:5]2[N:4]([CH3:21])[C:3](=[O:22])[CH:2]([NH:1][C:24]([NH:23][C:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([N:36]([CH3:38])[CH3:37])=[CH:28][CH:27]=3)=[S:25])[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[Cl:15])[C:6]=2[CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-amino-7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 8) (0.03 g, 1 mmol) in dichloroethane (5 ml) was added 4-isothiocyanato-N,N-dimethyl-1-naphthalenamine (0.025 g, 1 mmol). The reaction mixture was stirred at 70° C. for 4 hours. The solvent was evaporated in vacuo, the residue was triturated with ether and the title compound was obtained as a colorless solid (35 mg, 60%). 1H-NMR (CDCl3): δ 8.26 (d, J=8.4 Hz, 1H), 8.03 (d, J=7.6 Hz, 1H), 7.93 (br s, 1H), 7.73-7.06 (m, 11H) 6.10 (d, J=7.6 Hz, 1H), 3.40 (s, 3H) and 2.92 (s, 6H). MS (ESI) (M+H)+=562.

Workup

customThe solvent was evaporated in vacuo
customthe residue was triturated with ether

Sources & evidence

ORD record: ord-ed5bce2d98464265b221a150c48b5aa7
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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