Water → 3-[5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-5,5-dimethylhydantoin

HRID 354761Notes

Reaction equation

HRID 354761 reaction equation
[NH2:1][C:2]([CH3:29])([CH3:28])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH3:16])[C:14](=[O:17])[C:13]([CH3:19])([CH3:18])[N:12]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:10]=2[CH:27]=1)=[O:4].[C:30](Cl)(Cl)=[O:31].C(N(CC)CC)C.O>ClCCCl>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:11]1[C:10]2[CH:27]=[C:6]([N:5]3[C:3](=[O:4])[C:2]([CH3:29])([CH3:28])[NH:1][C:30]3=[O:31])[CH:7]=[CH:8][C:9]=2[N:15]([CH3:16])[C:14](=[O:17])[C:13]([CH3:19])([CH3:18])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 8471TriethylamineHCID 20506149HCID 20506149, compound

Product 1

HCID 205061833-[5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-5,5-dimethylhydantoin

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

2 g (0.005 mol) of 2 amino-N-[5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-2-methylpropionamide are dissolved in 50 ml of 1,2-dichloroethane and added to 1 g of phosgene in 50 ml of 1,2-dichloroethane at room temperature. The reaction mixture is stirred for 1/2 hour and subsequently made basic with triethylamine. The mixture is treated with water and extracted with methylene chloride. The organic phase is dried and evaporated. The residue gives, from ethyl acetate/ether, 3-[5-(o-fluorophenyl)-2,3-dihydro-1,3,3-trimethyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-5,5-dimethylhydantoin of melting point 286°-287°.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic phase is dried
  3. customevaporated

Sources & evidence

ORD record
ord-60969652dcb94f80a05a96160cfbba6f
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

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