Hydrochloric Acid → HCID 20562357, compound

HRID 848142Notes

Reaction equation

HRID 848142 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][C:12](=[O:33])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:34])[NH:10][CH2:11][C:12](=[O:33])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 20562364HCID 20562364, compound

Product 1

HCID 20562357HCID 20562357, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.5 g (0.0225 M) of benzyl{[[2-(o-fluorobenzoyl)-4-nitrophenyl]methylcarbamoyl]methyl}carbamate dissolved in 150 ml of glacial acetic acid are treated with 23 g of stannous chloride and 30 ml of mixture of concentrated hydrochloric acid and water (1:1). The mixture is stirred at room temperature for 20 hours, poured on to ice/ammonia and extracted several times with ethyl acetate. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is purified on a 350 g silica gel column using methylene chloride/ethyl acetate as the eluting agent and crystallised from methylene chloride/ether. There is obtained benzyl{[[4-amino-2-(o-fluorobenzoyl)phenyl]methylcarbamoyl]methyl}carbamate which melts at 83° C.

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialThe organic solution is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified on a 350 g silica gel column
  6. customcrystallised from methylene chloride/ether

Sources & evidence

ORD record
ord-6d59c424b4404391b94c6c5121876a13
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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