Chloroacetyl chloride → HCID 20554363, compound

HRID 1106030Notes

Reaction equation

HRID 1106030 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[N:13]1[C:18]2[NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[NH:22][C:23](=[O:24])[C:17]=2[CH:16]=[N:15][CH:14]=1>O1CCOCC1>[Cl:1][CH2:2][C:3]([N:19]1[C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[NH:22][C:23](=[O:24])[C:17]2[CH:16]=[N:15][CH:14]=[N:13][C:18]1=2)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 15535475HCID 15535475, compound

Product 1

HCID 20554363HCID 20554363, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 3.16 g (0.028 mol) of chloroacetyl chloride in 8 ml of absolute dioxan and a solution of 2.82 g (0.028 mol) of dry triethylamine in 6 ml of absolute dioxan are added dropwise, simultaneously and as uniformly as possible, in the course of 20 minutes, at 60° to 70° C., to a suspension of 4.24 g (0.02 mol) of 5,6-dihydropyrimido[4,5-b][1,5]benzodiazepin-5-one in 60 ml of absolute dioxan, while stirring. The mixture is heated under reflux for a further 4 hours; precipitated triethylamine hydrochloride is filtered off, and the filtrate is concentrated in vacuo. The residue is chromatographed on neutral silica gel, using chloroform; the eluate is evaporated and the residue therefrom is stirred with ether and, after filtration, recrystallized from ethanol; yield: 3.9 g, m.p. 196° C. (dec.), from isopropanol.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for a further 4 hours
  3. filtrationprecipitated triethylamine hydrochloride is filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is chromatographed on neutral silica gel
  6. customthe eluate is evaporated
  7. stirringthe residue therefrom is stirred with ether
  8. filtrationafter filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4c56d27596dd48528ba57fde3b4cede4
Source dataset
uspto-grants-1982_01
Patent number
US04311700

Reaction notes

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