Water → HCID 21265975, compound

HRID 566307Notes

Reaction equation

HRID 566307 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1.C(=O)([O-])O.[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[S:29])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:6]=2[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 21265985HCID 21265985, compound

Product 1

HCID 21265975HCID 21265975, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 3.45 g of 7-iodo-5-(2-pyridyl)-3H-1,4-benzodiazepin-2(1H)-one in 80 ml of hexamethylphosphoric acid triamide (HMPT) was treated with 4.24 g of Lawesson reagent and the mixture was stirred at 105° C. for 3.5 h. The reaction mixture was poured into 600 ml of saturated aqueous sodium hydrogen carbonate solution and 2 l of water. After stirring at room temperature for 30 min. the precipitate was filtered off. There were obtained 3.0 g of crude, yellow 7-iodo-5-(2-pyridyl)-3H-1,4-benzodiazepine-2(1H)-thione, m.p. 242° C., which was used in this form for the next step.

Workup

  1. stirringAfter stirring at room temperature for 30 min. the precipitate
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-a8e9289b72af48fdb3f40b4db6558960
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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