Sodium Carbonate → HCID 20562380, compound

HRID 1413775Notes

Reaction equation

HRID 1413775 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH:9]([CH2:14][CH3:15])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[CH:23]=1.[Cl:24]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])[CH:9]([CH2:14][CH3:15])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:6]=2[C:23]=1[Cl:24]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24526ChlorineHCID 20562360HCID 20562360, compound

Product 1

HCID 20562380HCID 20562380, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

13 g (0.042 M) of rac-7-amino-3-ethyl-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one are dissolved in 70 ml of concentrated hydrochloric acid at -10° C. and chlorine gas is then conducted in at -10° C. until the starting material can no longer be detected by thin-layer chromatography. The mixture is neutralised slowly with a mixture of ice and 10% sodium carbonate solution and the mixture is extracted several times with methylene chloride. The organic solution is washed with water, dried over sodium sulphate, filtered and concentrated. The residue is purified on a 300 g silica gel column with methylene chloride/ethyl acetate (10:1) and crystallised from ethanol. There is obtained rac-7-amino-3-ethyl-6-chloro-5-(o-fluorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one which melts at 250° C.

Workup

  1. customis then conducted in at -10° C. until the starting material
  2. extractionthe mixture is extracted several times with methylene chloride
  3. washThe organic solution is washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified on a 300 g silica gel column with methylene chloride/ethyl acetate (10:1)
  8. customcrystallised from ethanol

Sources & evidence

ORD record
ord-f1124a33fa10482bbabf50728a9594d1
Source dataset
uspto-grants-1981_02
Patent number
US04251443

Reaction notes

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