Sodium Hydroxide → (11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

HRID 895978Notes

Reaction equation

HRID 895978 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:28]=[CH:27][C:16]2[NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[NH:20][C:21](=[O:22])[C:15]=2[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>O1CCCC1.O>[O:22]=[C:21]1[NH:20][C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[NH:17][C:16]2[CH:27]=[CH:28][C:13]([NH:12][C:10]([NH2:9])=[S:11])=[CH:14][C:15]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117736461-Benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea

Product 1

HCID 11300593(11-Oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thioureaYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-benzoyl-3-(11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-2-yl)-thiourea (Example 8, 0.6 g, 1.54 mmol) in 10 mL of tetrahydrofuran was added 1.8 mL of 2.0 N aqueous sodium hydroxide. The mixture was heated to reflux for 3 hrs, diluted with water (10 mL) and extracted with ethyl acetate (3×100 mL). The combined organic fractions were dried with magnesium sulfate and concentrated under reduced pressure. The solid was washed with 1:1 ethyl acetate/hexanes (50 mL) to give a solid (yield 397 mg, 90.3%). H1 NMR (methanol d4) δ: 9.83 (s, 1H), 9.50 (s, 1H), 7.81 (s, 1H), 7.55-7.54 (d, 1H, J=1.9), 7.32-7.30 (m, 2H), 6.96-6.86 (m, 5H), 5.72 (s, 1H), MS (ES): MH+ 285.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hrs
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic fractions were dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe solid was washed with 1:1 ethyl acetate/hexanes (50 mL)

Sources & evidence

ORD record
ord-cf8fe4ad50c54ae2aaf2506267f158fb
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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