Ammonia → 5-(2-Chlorophenyl)-1,3-dihydro-7-iodo-2H-thieno[2,3-e]-1,4-diazepin-2-one

HRID 1032796Notes

Reaction equation

HRID 1032796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[CH:17][S:16][C:10]=2[NH:11][C:12](=[O:15])[CH2:13][N:14]=1.[I:19]Cl.C([O-])(=O)C.[Na+].S(=O)(O)[O-].[Na+].N>O.CO.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([I:19])[S:16][C:10]=2[NH:11][C:12](=[O:15])[CH2:13][N:14]=1

Participants

9

Reactant 5

HCID 222AmmoniaHCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 23665763Sodium BisulfiteHCID 1356185665-(2-chlorophenyl)-1,3-dihydro-2H-thieno(2,3-e)(1,4)diazepin-2-one

Product 1

HCID 1361324965-(2-Chlorophenyl)-1,3-dihydro-7-iodo-2H-thieno[2,3-e]-1,4-diazepin-2-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 54.8 g of 5-(2-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e][4,1]diazepin-2-one [NL patent 7,205,730, Nov. 1972, Hoffmann-La Roche & Co., AG, Basle]in 350 ml of acetic acid and 350 ml of methanol was treated with 64.4 g of iodine monochloride and 16.2 g of sodium acetate. The mixture was stirred for 15 minutes at room temperature. A solution of 65 g of sodium bisulfite in 350 ml of water was then added and stirring was continued for 10 minutes. The mixture was neutralized by addition of 500 ml of conc. ammonia and 1 kg of ice. The precipitated product was filtered off and washed with water and ethanol. Recrystallization from tetrahydrofuran/ ethanol gave off-white crystals of the title compound with m.p. 229°-231°.

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water and ethanol
  5. customRecrystallization from tetrahydrofuran/ ethanol

Sources & evidence

ORD record
ord-ee6d8915c18e412c9f642a523f4d489a
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

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