Dimethylformamide → HCID 135715021, compound

HRID 273784Notes

Reaction equation

HRID 273784 reaction equation
Cl[CH2:2][C:3]1[N:8]2[CH:9]=[N:10][N:11]=[C:7]2[C:6]2[S:12][CH:13]=[CH:14][C:5]=2[N:4]=1.CN(C)C=[O:18].[OH-].[Na+]>O1CCOCC1>[N:8]1[CH:9]=[N:10][N:11]2[C:7]=1[C:6]1[S:12][CH:13]=[CH:14][C:5]=1[NH:4][C:3](=[O:18])[CH2:2]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 20093979HCID 20093979, compound

Product 1

HCID 135715021HCID 135715021, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5. 15.2 g of 5-(chloromethyl)thieno[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine are suspended in 650 ml of dioxan and 43 ml of dimethylformamide and cooled to 5° C. 86 ml of 1N sodium hydroxide solution are added thereto within 3 min. and the mixture is stirred at room temperature for 17 h. The reaction mixture is then partitioned between 1.5 l of saturated aqueous sodium chloride solution and 0.7 l of chloroform. The aqueous phase is then made weakly acidic (pH 6) with 12N hydrochloric acid. The mixture is extracted five times with chloroform. The organic extracts are concentrated in a vacuum. The crystalline residue is recrystallized from ethanol. There is obtained 5H-thieno[2,3-f][1,2,4]triazolo[1,5-d][1,4]diazepin-6(7H)-one of m.p. 213°-215° C.

Workup

  1. customThe reaction mixture is then partitioned between 1.5 l of saturated aqueous sodium chloride solution and 0.7 l of chloroform
  2. extractionThe mixture is extracted five times with chloroform
  3. concentrationThe organic extracts are concentrated in a vacuum
  4. customThe crystalline residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-c4aef13f595e4521920499970005ecda
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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