Iodine → HCID 53912151, compound

HRID 1606979Notes

Reaction equation

HRID 1606979 reaction equation
[Br:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]3[CH2:18][CH2:17][CH2:16][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[I:20]I.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]3[CH2:18][CH2:17][CH2:16][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[I:20])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 11430Potassium CarbonateHCID 18634701HCID 18634701, compound

Product 1

HCID 53912151HCID 53912151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

15.90 g (50 mmol) of (S)-8-bromo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was stirred at 100° for 3 hours with 44 g (175 mmol) of iodine and 14 g (100 mmol) of potassium carbonate in 100 ml of N,N-dimethylformamide. The reaction mixture was poured into 1 l of water and, after stirring for 30 minutes, the precipitated product was filtered off. The filter residue was rinsed with water, dried and recrystallized from N,N-dimethylformamide. There was obtained (S)-8-bromo-11,12,13,13a-tetrahydro-1-iodo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 301°-303°.

Workup

  1. filtrationthe precipitated product was filtered off
  2. washThe filter residue was rinsed with water
  3. customdried
  4. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-4be6a3321dbb4e508baf2fbad8608f14
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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