Tetrahydrofuran → 2'-Iododiazepam

HRID 1586909Notes

Reaction equation

HRID 1586909 reaction equation
C1C[O:4]CC1.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH3:17])[CH2:15][CH2:14][N:13]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[I:24])[C:11]=2[CH:25]=1.C(=O)(O)[O-].[Na+].BrN1C(=O)CCC1=O>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[N:16]([CH3:17])[C:15](=[O:4])[CH2:14][N:13]=[C:12]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[I:24])[C:11]=2[CH:25]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 15615710HCID 15615710, compound

Product 1

HCID 1300622'-Iododiazepam

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A THF solution of 158 mg 7-chloro-2,3-dihydro-5-(2-iodophenyl)-1-methyl-1H-1,4-benzodiazepine and a sodium bicarbonate aqueous solution were simultaneously added by drops to a THF solution of N-bromosuccinimide at room temperature. After the mixture had been stirred at the same temperature for additional 30 minutes, water was poured thereinto and the resulting mixture was extracted with ethyl acetate. Purifying the crude product by silica gel column chromatography gave 140 mg of 2'-iododiazepam.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. customPurifying the crude product by silica gel column chromatography

Sources & evidence

ORD record
ord-4207fa38812444bf8efa7fc891a08902
Source dataset
uspto-grants-1993_06
Patent number
US05216147

Reaction notes

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