Dichloromethane → HCID 21317676, compound

HRID 262995Notes

Reaction equation

HRID 262995 reaction equation
[Cl:1][C:2]1[S:20][C:5]2[N:6]=[C:7]([NH:18][NH2:19])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1.[Cl:21][CH2:22][C:23](Cl)=O.C([O-])(=O)C.[Na+].C(Cl)Cl>C(O)(=O)C>[Cl:1][C:2]1[S:20][C:5]2[N:6]3[C:23]([CH2:22][Cl:21])=[N:19][N:18]=[C:7]3[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 213176957-Chloro-5-(2-chlorophenyl)-2-hydrazinyl-3H-thieno[2,3-e]-1,4-diazepine

Product 1

HCID 21317676HCID 21317676, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

0.7 g of 7-chloro-5-(o-chlorophenyl)-2-hydrazino-3H-thieno[2,3-e]-1,4-diazepine are introduced, with cooling at 15° C., into 15 ml of glacial acetic acid and a solution of 0.25 g of chloroacetyl chloride in 5 ml of glacial acetic acid is slowly added dropwise thereto. The mixture is then stirred for a further 2 hours, treated with 0.3 g of sodium acetate and stirred for 1 hour. The solution is poured on to ice-water, neutralized and shaken out with methylene chloride. After evaporation of the solvent, the residue is refluxed with 30 ml of absolute xylene for 1 hour. After evaporation of solvent, the residue is recrystallized from ethyl acetate containing active carbon to yield 2-chloro-9-chloromethyl-4-(o-chlorophenyl)-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine, melting point 101°-103° C.

Workup

  1. stirringstirred for 1 hour
  2. customAfter evaporation of the solvent
  3. temperaturethe residue is refluxed with 30 ml of absolute xylene for 1 hour
  4. customAfter evaporation of solvent
  5. customthe residue is recrystallized from ethyl acetate containing active carbon

Sources & evidence

ORD record
ord-008130abfdb34f56afb86683c7a7984d
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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