Methanol → Urea, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

HRID 848151Notes

Reaction equation

HRID 848151 reaction equation
C([N:8]([CH2:32][CH2:33][O:34]C(C)(C)C)[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][N:18]=[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[C:16]=2[CH:31]=1)=[O:10])C1C=CC=CC=1.C(=O)(O)[O-].[Na+].CO>Br>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:17]1[C:16]2[CH:31]=[C:12]([NH:11][C:9]([NH:8][CH2:32][CH2:33][OH:34])=[O:10])[CH:13]=[CH:14][C:15]=2[N:21]([CH3:22])[C:20](=[O:23])[CH2:19][N:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 20562388HCID 20562388, compound

Product 1

HCID 3058284Urea, N-(5-(2-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl)-N(sup 1)-(2-hydroxyethyl)-

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1.5 g (0.003 M) of 1-benzyl-1-(2-tert.butoxyethyl)-3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]urea are dissolved in 15 ml of 48% aqueous hydrogen bromide solution, the mixture is heated on a steam-bath for 10 minutes, made alkaline with sodium bicarbonate, treated with a small amount of methanol and extracted three times with methylene chloride. The extracts are combined, dried over sodium sulphate, filtered and concentrated. The residue is purified in a pressure column (0.2-0.4 atmospheres of nitrogen) on 300 g of silica gel (particle size 0.04-0.06 mm) using acetone as the eluting agent and crystallised from acetone/ether. There is obtained 1-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]-3-(2-hydroxyethyl)urea which, according to the IR spectrum, is identical with a sample of this substance prepared in another manner (see Example 7).

Workup

  1. temperaturethe mixture is heated on a steam-bath for 10 minutes
  2. extractionextracted three times with methylene chloride
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified in a pressure column (0.2-0.4 atmospheres of nitrogen) on 300 g of silica gel (particle size 0.04-0.06 mm)
  7. customcrystallised from acetone/ether

Sources & evidence

ORD record
ord-34796769235c4b9d89b1ec48b3473090
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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