Chlorosuccinimide → HCID 14854874, compound

HRID 330468Notes

Reaction equation

HRID 330468 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH2:17][N:16]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[CH:27]=[C:15]3[C:14]=2[CH:28]=1>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18](=[O:20])[CH2:17][N:16]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:27]([Cl:1])=[C:15]3[C:14]=2[CH:28]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 14854877HCID 14854877, compound

Product 1

HCID 14854874HCID 14854874, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.08 g N-chlorosuccinimide in 50 ml dimethylformamide was added dropwise at 15° C. to a solution of 4.00 g 2-chloroindolo[1,2-d][1,4]benzodiazepin-6(7H)-one in 125 ml dimethylformamide. The solution was stirred for two hours at room temperature. Upon dilution with water, a solid precipitated, which was collected and washed with hexane. Recrystallization from toluene yielded 2.67 g solid, m.p. 267°-271° C.

Workup

  1. customUpon dilution with water, a solid precipitated
  2. customwhich was collected
  3. washwashed with hexane
  4. customRecrystallization from toluene

Sources & evidence

ORD record
ord-efde44cf81db4986a5e1fc28a7fdd4d2
Source dataset
uspto-grants-1990_01
Patent number
US04897392

Reaction notes

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