Chlorosuccinimide → HCID 178494428, compound

HRID 231308Notes

Reaction equation

HRID 231308 reaction equation
[NH:1]([C:5]1[CH:15]=[C:14]2[C:8]([CH:9]=[C:10]([O:16][CH3:17])[O:11][C:12]2=[O:13])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3].[Cl:18]N1C(=O)CCC1=O>CN(C=O)C>[NH:1]([C:5]1[CH:15]=[C:14]2[C:8]([C:9]([Cl:18])=[C:10]([O:16][CH3:17])[O:11][C:12]2=[O:13])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178486624HCID 178486624, compound

Product 1

HCID 178494428HCID 178494428, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.27 g of 7-guanidino-3-methoxyisocoumarin (1 mmole) was chlorinated with 0.15 g of N-chlorosuccinimide (1.1 mmole) in 5 ml DMF at r.t. overnight. The reaction mixture was evaporated to dryness, and purified by silica gel column chromatography which is eluted with methylene chloride and methanol (5:1) to give 0.1 g of 7-guanidino-3-methoxy-4-chloroisocoumarin (yield 34%). One spot on TLC, Rf =0.75 (Butanol:acetic acid:pyridine:water=4:1:1:2); NMR spectrum is similar to 7-guanidino-3-methoxyisocoumarin except no peak at 6.1 ppm; mass spectrum (FAB+), m/e=268 (M+ -Cl). Anal. Calc. for C11H11N3O3Cl2.1/2H2O: C, 42.17; H, 3.83; N, 13.41; Cl, 22.68. Found: C, 42.65; H, 3.72; N, 13,28; Cl, 22.32.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by silica gel column chromatography which
  3. washis eluted with methylene chloride and methanol (5:1)

Sources & evidence

ORD record
ord-e55fb0bcc39e41d2ab67e41736f58aba
Source dataset
uspto-grants-1989_07
Patent number
US04845242

Reaction notes

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