Sodium Carbonate → HCID 20562334, compound

HRID 848120Notes

Reaction equation

HRID 848120 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[CH:21]=1.[Cl:22]Cl.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]=2[C:21]=1[Cl:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 922947-Aminoflunitrazepam

Product 1

HCID 20562334HCID 20562334, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

80 g (0.28 M) of 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one are dissolved in 220 ml of concentrated hydrochloric acid and chlorine gas is slowly conducted into the solution at -10° C. for 4 hours. The mixture is slowly poured on to a mixture of ice and sodium carbonate solution (250 g of sodium carbonate dissolved in water) and extracted with methylene chloride. The extract is dried over sodium sulphate, filtered and concentrated. The residue is purified on a 1.2 kg silica gel column using methylene chloride and then methylene chloride/ethyl acetate (10:1) as the eluting agent and crystallised from ethyl acetate/ether/n-hexane. There is obtained 7-amino-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one which melts at 240° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified on a 1.2 kg silica gel column
  6. custommethylene chloride/ethyl acetate (10:1) as the eluting agent and crystallised from ethyl acetate/ether/n-hexane

Sources & evidence

ORD record
ord-9dc70cbd4c8c472d914f06c83cd3dea0
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

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