Water → 1-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 68941Notes

Reaction equation

HRID 68941 reaction equation
B(Br)(Br)Br.ClCCl.ClCCl.[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([O:29]C)[CH:27]=[CH:28][C:14]1=2)[CH3:12].O>ClCCl.CO.CO>[CH2:11]([N:13]1[C:19](=[O:20])[C:18]([CH3:22])([CH3:21])[C:17](=[O:23])[N:16]([CH3:24])[C:15]2[CH:25]=[C:26]([OH:29])[CH:27]=[CH:28][C:14]1=2)[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 22277759Boron tribromide dichloromethaneHCID 686743071-Ethyl-7-methoxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 686733851-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 97.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

1.0M-boron tribromide/dichloromethane solution (1.22 ml) was added to a dichloromethane solution (3 ml) of 1-ethyl-7-methoxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (169 mg) at 0° C. The mixture was stirred at room temperature overnight. Water and methanol were added to the reaction mixture, and extraction was performed using a dichloromethane/methanol mixture (dichloromethane:methanol=10:1). The organic layer was dried over anhydrous sodium sulfate, and condensed to dryness under reduced pressure to give the title compound (156.4 mg) as a white powder.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate, and condensed to dryness under reduced pressure

Sources & evidence

ORD record
ord-9f866d02a8014aba85fdf27de5334129
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…