Acetyl chloride → HCID 12434322, compound

HRID 262981Notes

Reaction equation

HRID 262981 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:19]=[CH:18][S:17][C:10]=2[N:11]=[C:12]([NH:15][NH2:16])[CH2:13][N:14]=1.C(=O)(O)[O-].[Na+].[C:25](Cl)(=O)[CH3:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[CH:18][S:17][C:10]=2[N:11]2[C:25]([CH3:26])=[N:16][N:15]=[C:12]2[CH2:13][N:14]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 12434297HCID 12434297, compound

Product 1

HCID 12434322HCID 12434322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2 g (0.0069 mol) of 5-(o-chlorophenyl)-2-hydrazino-3H-thieno[2,3-e]-1,4-diazepine are suspended in 200 ml of dry methylene chloride and treated with 10 g of sodium bicarbonate. The solution is cooled to 0° C. and treated with stirring with 0.8 ml of acetyl chloride. After 45 minutes, the solid material is filtered off from the solution which is then shaken out twice with 100 ml of water each time. After drying over sodium sulphate, the organic phase is evaporated and treated with 100 ml of butanol, whereupon 20 ml thereof are evaporated off under reduced pressure. The solution is refluxed for 8 hours and evaporated under vacuum. After trituration of the oily residue with ethanol, the resulting crystals are refluxed with a small amount of ethanol, left to crystallize in a refrigerator, filtered under a vacuum and dried to yield 4-(o-chlorophenyl)-9-methyl-6H-thieno[3,2-f]-s-triazolo[4,3-a][1,4]diazepine, melting point 221°-223° C.

Workup

  1. additiontreated
  2. filtrationthe solid material is filtered off from the solution which
  3. dry with materialAfter drying over sodium sulphate
  4. customthe organic phase is evaporated
  5. additiontreated with 100 ml of butanol, whereupon 20 ml
  6. customthereof are evaporated off under reduced pressure
  7. temperatureThe solution is refluxed for 8 hours
  8. customevaporated under vacuum
  9. temperatureAfter trituration of the oily residue with ethanol, the resulting crystals are refluxed with a small amount of ethanol
  10. waitleft
  11. customto crystallize in a refrigerator
  12. filtrationfiltered under a vacuum
  13. customdried

Sources & evidence

ORD record
ord-4fc64f1c915f4f1298a53fb54c4542ce
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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