Sodium Hydroxide → HCID 11449002, compound

HRID 895983Notes

Reaction equation

HRID 895983 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]2[O:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[NH:19][C:18](=[O:27])[C:17]=2[CH:28]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1>[O:27]=[C:18]1[C:17]2[CH:28]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[CH:14]=[CH:15][C:16]=2[O:22][C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[NH:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11303821HCID 11303821, compound

Product 1

HCID 11449002HCID 11449002, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-benzoyl-3-(11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepin-2-yl)-thiourea (Example 15) in 15 mL of THF was added 1.0 mL of 2.0 N aqueous sodium hydroxide. The resulting solution was heated for 3 hr under reflux. The mixture was concentrated and the residue was triturated with 50 mL of a 10% THF:90% dichloromethane solution. The solid was filtered and washed with 30 mL of water (yield 201 mg, 78%). H1 NMR (CDCl3) δ: 10.3 (bs, 1H), 7.74-7.61 (m, 3H), 7.28-7.15 (m, 3H), MS (ES): MH+ 286.1.

Workup

  1. temperatureThe resulting solution was heated for 3 hr
  2. temperatureunder reflux
  3. concentrationThe mixture was concentrated
  4. customthe residue was triturated with 50 mL of a 10% THF
  5. filtrationThe solid was filtered
  6. washwashed with 30 mL of water (yield 201 mg, 78%)

Sources & evidence

ORD record
ord-7457771ac8984bfda3271f155e300e87
Source dataset
uspto-grants-2005_07
Patent number
US06919328B1

Reaction notes

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