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

HRID 1702448Notes

Reaction equation

HRID 1702448 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=12.[Cl:17][CH2:18][C:19](Cl)=[O:20]>O1CCOCC1>[Cl:17][CH2:18][C:19]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2=[CH:4][S:3][C:2]([CH3:1])=[C:6]12)=[O:20]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 126587009,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 198042184-chloroacetyl-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8 g of 9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one and 5.6 ml of chloroacetyl chloride are boiled in 160 ml of dioxane (containing 8 g of ground potassium carbonate) under reflux for 8 hours. The thus-obtained suspension is concentrated to dryness; the resulting 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 dried toluene solution yields 4-chloroacetyl-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one (m. 156° to 158° C.).

Workup

  1. temperatureunder reflux for 8 hours
  2. concentrationThe thus-obtained suspension is concentrated to dryness
  3. washthe toluene mixture is washed with sodium bicarbonate solution
  4. dry with materialwith water, and the toluene solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-46f48a9ee2c646548adb6318533a44d7
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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