Benzoyl isothiocyanate → 1-Benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

HRID 895977Notes

Reaction equation

HRID 895977 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[C:18]([N:26]=[C:27]=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:18]([NH:26][C:27]([NH:1][C:2]1[CH:17]=[CH:16][C:5]2[NH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1)=[S:28])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 107755612-Amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 117736461-Benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2-amino-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one (Example 6, 0.5 g, 2.22 mmol) in 20 mL of THF was cooled to 0° C. (ice/water bath). Benzoyl isothiocyanate was added dropwise over a period of 10 min. The mixture was warmed to room temperature and stirred for 20 hr. The solvent was evaporated and the yellow solid washed with 50 mL of 1:1 ethyl acetate/hexanes solution (yield 0.736 g, 85%). H1 NMR (DMSO d6) δ: 12.43 (s, 1H), 11.53 (s, 1H), 9.92 (s, 1H), 8.00-7.95 (m, 3H), 7.06-6.96 (m, 6H), MS (ES): MH+ 389.1.

Workup

  1. customThe solvent was evaporated
  2. washthe yellow solid washed with 50 mL of 1:1 ethyl acetate/hexanes solution (yield 0.736 g, 85%)

Sources & evidence

ORD record
ord-db451650b88b451d920a7735a0f1cbd8
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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