Hydrogen Bromide → HCID 20562331, compound

HRID 848149Notes

Reaction equation

HRID 848149 reaction equation
C([N:8]([CH2:32][CH2:33][O:34][C:35]([CH3:38])(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.Br.C(=O)(O)[O-:41].[Na+]>C(O)(=O)C>[C:35]([O:34][CH2:33][CH2:32][NH:8][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])(=[O:41])[CH3:38]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 20562388HCID 20562388, compound

Product 1

HCID 20562331HCID 20562331, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

200 mg (0.4 mM) 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 heated on a steam-bath for 10 minutes in 3 ml of a 33% solution of hydrogen bromide in glacial acetic acid and then left to stand at room temperature for 3 days. The mixture is neutralised with sodium bicarbonate and extracted several times with methylene chloride. The methylene chloride 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 15 g of silica gel (particle size 0.04-0.06 mm) using ethyl acetate as the eluting agent and crystallised from ethyl acetate/ether, there being obtained 2-[3-[5-(o-fluorophenyl)-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-7-yl]ureido]ethyl acetate which melts at 196°-198° C.

Workup

  1. waitleft
  2. extractionextracted several 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 15 g of silica gel (particle size 0.04-0.06 mm)
  7. customcrystallised from ethyl acetate/ether, there

Sources & evidence

ORD record
ord-067fcd5c283443f9af14969f981019cc
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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