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

HRID 2223062Notes

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]([CH2:20][CH:21]=[CH2:22])[C:3]1=[O:23].[N:24]([C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([N:37]([CH3:39])[CH3:38])=[CH:29][CH:28]=1)=[C:25]=[S:26]>ClC(Cl)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:5]2[N:4]([CH2:20][CH:21]=[CH2:22])[C:3](=[O:23])[CH:2]([NH:1][C:25]([NH:24][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:30]([N:37]([CH3:39])[CH3:38])=[CH:29][CH:28]=3)=[S:26])[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

Conditions

Temperature: 70 °C

Procedure

A solution of 3-amino-7-chloro-1,3-dihydro-5-phenyl-1-(2-propenyl)-2H-1,4-benzodiazepin-2-one (INTERMEDIATE 6) (0.162 g, 0.5 mmol) in dichloroethane (5 ml) was added 4-isothiocyanato-N,N-dimethyl-1-naphthalenamine (0.115 g, 0.5 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 (0.152 g, 55%). 1H-NMR (CDCl3): δ 8.29-8.27 (m, 1H), 8.08-8.06 (m, 1H), 7.90 (s, 1H), 7.60-7.36 (m, 10H), 7.32 (d, J=2.4 Hz, 1H), 7.09 (d, J=8 Hz, 1H), 6.14 (d, J=7.6 Hz, 1H), 5.76-5.69 (m, 1H), 5.15 (s, 1H), 5.12 (dd, J=1.2 and 7.0 Hz, 1H), 4.57-4.39 (m, 2H) and 2.93 (s, 6H). MS (ESI) (M+H)+=554.

Workup

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

Sources & evidence

ORD record: ord-d8f2221ddd2e441699a9b677da299a6c
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375101B2

Reaction notes

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