Chloroacetyl chloride → HCID 20554414, compound

HRID 1106033Notes

Reaction equation

HRID 1106033 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:12]([N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:17]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:27]=[CH:28][C:16]=2[C:15]1=[O:35])[CH3:13]>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:18]1[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:14]([CH2:12][CH3:13])[C:15](=[O:35])[C:16]2[CH:28]=[N:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][C:17]1=2)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 20554331HCID 20554331, compound

Product 1

HCID 20554414HCID 20554414, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

28 g (250 mmol) of chloroacetyl chloride and 28 g (250 mmol) of sodium carbonate are added to a solution of 20 g (63 mmol) of 6-ethyl-2-phenyl-5,6-dihydropyrimido[4,5-b][1,5]benzodiazepin-5-one in 500 ml of absolute toluene. The mixture is stirred for 20 hours at 100° C. The solvent is removed on a rotary evaporator, and the residue is neutralized with 2 N-hydrochloric acid. The mixture is extracted with chloroform, and the organic phase is washed with water, dried and concentrated in vacuo. The residue which remains is recrystallized from isopropanol; yield: 19.2 g (77%), m.p. 147° to 148° C.

Workup

  1. customThe solvent is removed on a rotary evaporator
  2. extractionThe mixture is extracted with chloroform
  3. washthe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue which remains is recrystallized from isopropanol

Sources & evidence

ORD record
ord-9ef614ba41ce4222a77eb12fe7eb899b
Source dataset
uspto-grants-1982_01
Patent number
US04311700

Reaction notes

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