Chloroacetyl chloride → HCID 21414251, compound

HRID 442326Notes

Reaction equation

HRID 442326 reaction equation
[O-2].[Mg+2].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:7][CH2:6][C:5]1=[O:22].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=2[CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]([C:25](=[O:26])[CH2:24][Cl:23])[CH2:6][C:5]1=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 30819844,5-DihydrodiazepamHCID 6850729Magnesium monoxide

Product 1

HCID 21414251HCID 21414251, compoundYield 8.14%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3 g. of magnesium oxide are added to a solution of 2.87 g. (0.01 mmoles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2 H-1,4-benzodiazepine-2-one in 30 ml. of chloroform, and a solution of 1.2 ml. (0.018 moles) of chloroacetyl chloride in 4 ml. of chloroform is added to the vigorously stirred mixture. After 3 hours of stirring at room temperature the magnesium salt is filtered off, washed with 20 ml. of chloroform, and the filtrate is evaporated to dryness under reduced pressure. The residue is crystallized from acetone. 2.68 g. (8.14 %) of 1-methyl-4-chloroacetyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 197°-200° C.; Rf2 = 0.5.

Workup

  1. filtrationis filtered off
  2. washwashed with 20 ml
  3. customof chloroform, and the filtrate is evaporated to dryness under reduced pressure
  4. customThe residue is crystallized from acetone

Sources & evidence

ORD record
ord-35ae73e7c4a24330bcf93181976dca51
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

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