Iodine → HCID 54331352, compound

HRID 1607022Notes

Reaction equation

HRID 1607022 reaction equation
[CH:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[N:7]3[CH2:16][CH2:17][CH2:18][C@H:6]3[C:5]=12.[I:19]I>CN(C)C=O>[I:19][C:1]1[N:2]=[CH:3][N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[N:7]3[CH2:16][CH2:17][CH2:18][C@H:6]3[C:5]=12

Participants

4

Reactant 2

HCID 807IodineHCID 54051837HCID 54051837, compound

Product 1

HCID 54331352HCID 54331352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44.26 g (185 mmol) of (S)-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one was stirred at 100° for 4 hours with 162.8 g (645 mmol) of iodine in 300 ml of N,N-dimethylformamide. The reaction mixture was evaporated, the residue was taken up in water and methylene chloride, decolorized with sodium thiosulphate and neutralized with sodium bicarbonate. The aqueous phase was separated and extracted four times with methylene chloride. The combined organic phases were dried over magnesium sulphate and evaporated. By chromatography of the crude product on silica gel while eluting with ethyl acetate and subsequent recrystallization from methylene chloride and methanol there was obtained (S)-11,12,13,13a-tetrahydro-1-iodo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-9-one of melting point 222°-223°.

Workup

  1. customThe reaction mixture was evaporated
  2. customThe aqueous phase was separated
  3. extractionextracted four times with methylene chloride
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customevaporated
  6. washBy chromatography of the crude product on silica gel while eluting with ethyl acetate and subsequent recrystallization from methylene chloride

Sources & evidence

ORD record
ord-8345cdd0b5c649d48e8c27fd4ad9e4bb
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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