Ammonia → HCID 21265962, compound

HRID 566297Notes

Reaction equation

HRID 566297 reaction equation
[NH3:1].[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:15]2[CH:16]=[C:17]([I:20])[CH:18]=[CH:19][C:14]=2[NH:13][C:12](=S)[CH2:11][N:10]=1.CO>O1CCCC1>[NH2:1][C:12]1[CH2:11][N:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[C:15]2[CH:16]=[C:17]([I:20])[CH:18]=[CH:19][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 14851833HCID 14851833, compound

Product 1

HCID 21265962HCID 21265962, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50 ml of 25% aqueous ammonia solution were added to a solution of 2.3 g of 5-(2-fluorophenyl)-7-iodo-3H-1,4-benzodiazepine-2(1H)-thione (A. Walser, T. Flynn, C. Mason, H. Crowley, C. Maresco, B. Yaremko & M. O'Donell, J.Med.Chem., 1991, 34, 1209) in 120 ml of tetrahydrofuran. After the addition of 5 ml of methanol the solution was stirred at room temperature for 24 h. and then evaporated in a vacuum. The residue was partitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform. The aqueous phase was extracted a further three times with chloroform. The chloroform extracts were dried over sodium sulphate and evaporated in a vacuum. The residue was recrystallized from ethyl acetate. There were obtained 2.73 g of 2-amino -7-iodo-5-(2-fluorophenyl)-3H-1,4-benzodiazepine of m.p. 219-221° C.

Workup

  1. customevaporated in a vacuum
  2. customThe residue was partitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform
  3. extractionThe aqueous phase was extracted a further three times with chloroform
  4. dry with materialThe chloroform extracts were dried over sodium sulphate
  5. customevaporated in a vacuum
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ced094a965d647829914eb88f319ede1
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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