Ethyl chloroformate → 9-ethoxycarbonylaminomethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

HRID 262989Notes

Reaction equation

HRID 262989 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]2[C:8]3[S:22][C:21]([Cl:23])=[CH:20][C:9]=3[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N:11][CH2:12][C:6]2=[N:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30]([O:32][C:33](Cl)=[O:34])[CH3:31]>O1CCOCC1>[CH2:30]([O:32][C:33]([NH:1][CH2:2][C:3]1[N:7]2[C:8]3[S:22][C:21]([Cl:23])=[CH:20][C:9]=3[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])=[N:11][CH2:12][C:6]2=[N:5][N:4]=1)=[O:34])[CH3:31]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 191305Ro 11-7800

Product 1

HCID 213177059-ethoxycarbonylaminomethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.6 g of 9-aminomethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine are dissolved in 15 ml of absolute dioxane. 1.5 g of potassium carbonate are suspended in the solution and 0.18 g of chloroformic acid ethyl ester added with stirring. After 3 hours, the solid material is filtered off from the solution. The residue obtained after evaporation of the filtrate is recrystallized from ethyl acetate containing active carbon, to yield 9-ethoxycarbonylaminomethyl-2-chloro-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine.

Workup

  1. additionadded
  2. filtrationthe solid material is filtered off from the solution
  3. customThe residue obtained
  4. customafter evaporation of the filtrate
  5. customis recrystallized from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-9f776b325ca74b058d562d8f350d6d07
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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