Chloroacetyl chloride → 4-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one

HRID 2058602Notes

Reaction equation

HRID 2058602 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[CH3:13][N:14]1[C:23]2[C:22](=[O:24])[NH:21][C:20]3[CH:25]=[CH:26][CH:27]=[CH:28][C:19]=3[NH:18][C:17]=2[C:16]([CH3:29])=[N:15]1>O1CCOCC1>[Cl:1][CH2:2][C:3]([N:18]1[C:19]2[CH:28]=[CH:27][CH:26]=[CH:25][C:20]=2[NH:21][C:22](=[O:24])[C:23]2[N:14]([CH3:13])[N:15]=[C:16]([CH3:29])[C:17]1=2)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 205498761,3-Dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one

Product 1

HCID 205498784-Chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-oneYield 65.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2 g of chloroacetyl chloride and 2 g of triethylamine are added dropwise at the same time over the course of 40 minutes to a boiling solution of 2.3 g of 1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one in 30 ml of absolute dioxane, 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 and chromatographed over a silica gel column by means of a 1:1 mixture of petroleum ether and ethyl acetate, and the product is recrystallized from toluene to yield 2.0 g of 4-chloroacetyl-1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one, mp 246° to 248° C. (dec.).

Workup

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

Sources & evidence

ORD record
ord-4abf9a9fb9ff47d9bbecf63364e27b8b
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

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