Chloroacetyl chloride → HCID 20554401, compound

HRID 1106031Notes

Reaction equation

HRID 1106031 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]2[N:18]=[CH:19][N:20]=[CH:21][C:9]=2[C:8]1=[O:22]>O1CCOCC1.N1C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:7]([CH3:6])[C:8](=[O:22])[C:9]2[CH:21]=[N:20][CH:19]=[N:18][C:10]1=2)=[O:4]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 15535476HCID 15535476, compound

Product 1

HCID 20554401HCID 20554401, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent3×

Procedure

6.25 g (0.044 mol) of chloroacetyl chloride in 15 ml of absolute dioxan and 4.4 ml of dry pyridine in 15 ml of dioxan are added dropwise simultaneously (at 80° C. and in the course of 20 minutes) to a suspension of 4.6 g (0.020 mol) of 6-methyl-5,6-dihydropyrimido[4,5-b][1,5]benzodiazepin-5-one in 35 ml of absolute dioxan. The mixture is heated at the boil for a further 15 minutes and is then allowed to cool. The supernatant liquid is decanted off from the heavy dark phase, and the latter is washed with methylene chloride; the dioxan and methylene chloride phases are concentrated in vacuo. The oil which remains is dissolved in a little chloroform and filtered through neutral silica gel; the filtrate is evaporated and the residue is recrystallized from isopropanol, yield: 2.8 g, m.p. 176° to 178° C. (dec.).

Workup

  1. temperatureThe mixture is heated at the boil for a further 15 minutes
  2. temperatureto cool
  3. customThe supernatant liquid is decanted off from the heavy dark phase
  4. washthe latter is washed with methylene chloride
  5. concentrationthe dioxan and methylene chloride phases are concentrated in vacuo
  6. dissolutionThe oil which remains is dissolved in a little chloroform
  7. filtrationfiltered through neutral silica gel
  8. customthe filtrate is evaporated
  9. customthe residue is recrystallized from isopropanol, yield: 2.8 g, m.p. 176° to 178° C. (dec.)

Sources & evidence

ORD record
ord-67b563c655d4460d91d14064a35be7de
Source dataset
uspto-grants-1982_01
Patent number
US04311700

Reaction notes

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