Chloroacetyl chloride → HCID 13578543, compound

HRID 465057Notes

Reaction equation

HRID 465057 reaction equation
[Cl:1][C:2]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[N:4]([CH3:17])[CH:3]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21]>C(#N)C>[Cl:1][C:2]1[C:6]2[N:7]([C:20](=[O:21])[CH2:19][Cl:18])[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[NH:10][C:11](=[O:12])[C:5]=2[N:4]([CH3:17])[CH:3]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 13578542HCID 13578542, compound

Product 1

HCID 13578543HCID 13578543, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

First, 3-chloro-1-methyl-1,4,9,10-tetrahydropyrrolo[3,2-b]-[1,5]benzodiazepin-10-one (1.7 g, 6.86 mmol), is refluxed for 1 hour in a mixture with acetonitrile (50 ml) and chloroacetyl chloride (4.0 ml, 52.9 mmol). The mixture is concentrated in vacuo, the residue is taken up in water (20 ml) and filtered and the solid residue is chromatographed using dichloromethane/cyclohexane/ethyl acetate (1:2:1 v/v) as eluant. A wine-red solid is isolated from the eluate, yielding colorless crystals (1.4 g) of mp. 284°-285° C. (D) after purification with tert.butyl methyl ether.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. filtrationfiltered
  3. customthe solid residue is chromatographed
  4. customA wine-red solid is isolated from the eluate,

Sources & evidence

ORD record
ord-144aa9f1ff2e428da39185c1c74e4476
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

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