1,3-Dichloroacetone → HCID 21265995, compound

HRID 566277Notes

Reaction equation

HRID 566277 reaction equation
[C:1]1([C:7]2[C:8]3[S:17][CH:16]=[CH:15][C:9]=3[N:10]=[C:11]([NH2:14])[CH2:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](=[O:21])(O)[O-].[Na+].Cl[CH2:24][C:25](CCl)=O.[OH-].[Na+]>O1CCOCC1>[C:1]1([C:7]2[C:8]3[S:17][CH:16]=[CH:15][C:9]=3[N:10]3[CH:24]=[C:25]([CH2:18][OH:21])[N:14]=[C:11]3[CH2:12][N:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 107931,3-DichloroacetoneHCID 14798Sodium Hydroxide2×HCID 516892Sodium BicarbonateHCID 21266002HCID 21266002, compound

Product 1

HCID 21265995HCID 21265995, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2.9 g of 5-phenyl-3H-thieno[3,2-e][1,4]diazepin-2-ylamine, 11.7 g of sodium bicarbonate and 1.83 g of 1,3-dichloroacetone in 80 ml of dioxan was stirred at room temperature under argon for 48 h. Thereafter, the temperature of the reaction mixture was increased to 80° C. and the suspension was stirred under argon for a further 27 h. After cooling to 60° C. 19.2 g of 2.5N sodium hydroxide solution were added and the reaction mixture was stirred under argon for a further 20 h. Subsequently, a further two 19.2 g portions of 2.5N sodium hydroxide solution were added at intervals of twenty hours. The suspension was extracted with dichloromethane/saturated sodium chloride solution in the presence of a small amount of methanol. The dichloromethane extracts were dried with sodium sulphate, filtered and evaporated in a vacuum. The residue was suspended twice in succession in methanol and triturated. There were obtained 2.14 g of crude 4-phenyl-6H-imidazo[1,2-a]thieno[2,3-f][1,4]diazepin-8-ylmethanol which was used without further purification as the free base for the preparation of the dihydrochloride.

Workup

  1. temperatureThereafter, the temperature of the reaction mixture was increased to 80° C.
  2. stirringthe suspension was stirred under argon for a further 27 h
  3. temperatureAfter cooling to 60° C
  4. stirringthe reaction mixture was stirred under argon for a further 20 h
  5. extractionThe suspension was extracted with dichloromethane/saturated sodium chloride solution in the presence of a small amount of methanol
  6. dry with materialThe dichloromethane extracts were dried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated in a vacuum
  9. customtriturated

Sources & evidence

ORD record
ord-69fce56a120145b1a5fbd12bff1ef98c
Source dataset
uspto-grants-2001_01
Patent number
US06174881B1

Reaction notes

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