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

HRID 1702450Notes

Reaction equation

HRID 1702450 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[CH:13]1[S:14][CH:15]=[C:16]2[C:22]=1[C:21](=[O:23])[NH:20][C:19]1[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=1[NH:17]2>O1CCOCC1>[Cl:1][CH2:2][C:3]([N:17]1[C:18]2[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=2[NH:20][C:21](=[O:23])[C:22]2=[CH:13][S:14][CH:15]=[C:16]12)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 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-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.2 g of chloroacetyl chloride and 2 ml of triethylamine are simultaneously added dropwise to a boiling solution of 2.2 g of 9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one in 30 ml of absolute dioxane in the course of 40 minutes, and the mixture is stirred for a further 3 hours. It is then allowed to cool and is filtered; the filtrate is concentrated to dryness; the residue is chromatographed over a silica gel column by means of a mixture of petroleum ether/ethyl acetate (1:1), and the product is recrystallized from toluene to yield 2.0 g of 4-chloroacetyl-9,10-dihydro-4H-thieno[3,4-b][1,5]benzodiazepin-10-one (m. 220° C.).

Workup

  1. temperatureto cool
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated to dryness
  4. customthe residue is chromatographed over a silica gel column by means of a mixture of petroleum ether/ethyl acetate (1:1)
  5. customthe product is recrystallized from toluene

Sources & evidence

ORD record
ord-8dfde1ca31fa49838ffae803033b04de
Source dataset
uspto-grants-1983_04
Patent number
US04381301

Reaction notes

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