Chloroacetyl chloride → 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1702449Notes

Reaction equation

HRID 1702449 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH:6]1[S:7][CH:8]=[C:9]2[C:15]=1[C:14](=[O:16])[NH:13][C:12]1[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=1[NH:10]2>O1CCOCC1>[Cl:1][CH2:2][C:3]([N:10]1[C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[NH:13][C:14](=[O:16])[C:15]2=[CH:6][S:7][CH:8]=[C:9]12)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 200638994-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.4 ml of chloroacetyl chloride are added dropwise at room temperature to a suspension of 18.8 g of 9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one in 500 ml of dioxane, whereupon a clear solution is formed. The solution is left to stand for 3 hours and is then concentrated to dryness; the obtained residue is taken up in toluene; the toluene mixture is washed with sodium bicarbonate solution and then with water, and the toluene solution is dried over sodium sulfate. Concentration of the thus-dried solution yields 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one (m. 220° C.).

Workup

  1. customis formed
  2. waitThe solution is left
  3. concentrationis then concentrated to dryness
  4. washthe toluene mixture is washed with sodium bicarbonate solution
  5. dry with materialwith water, and the toluene solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-ac3105611a8444ac9562be28aa55dde7
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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