Chlorosuccinimide → trans-4-[N-(2-chloro-3-oxo-cyclopent-1-enyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1460620Notes

Reaction equation

HRID 1460620 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8][C:9]2[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=2)[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]1([CH3:22])[CH3:21].[Cl:23]N1C(=O)CCC1=O>ClCCl.O1CCOCC1>[Cl:23][C:10]1[C:11](=[O:14])[CH2:12][CH2:13][C:9]=1[NH:8][C@@H:7]1[C:6]2[CH:15]=[C:16]([C:19]#[N:20])[CH:17]=[CH:18][C:5]=2[O:4][C:3]([CH3:22])([CH3:21])[C@H:2]1[OH:1]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 14301304trans-3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(3-oxo-1-cyclopent-1-enylamino)-2H-1-benzopyran-6-carbonitrile

Product 1

HCID 14301326trans-4-[N-(2-chloro-3-oxo-cyclopent-1-enyl)amino]-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 150 mg of the title compound of example 5 in 5 ml of dichloromethan and 5 ml of dioxan is mixed with 77 mg of N-chloro-succinimide. After 50 minutes at room temperature the solution is poured on water and the organic components are extracted with dichloromethane/ethanol. Recristallisation of the raw product obtained after concentration yields white crystalls of the title compound having a m.p. of 288°-89° C.

Workup

  1. additionAfter 50 minutes at room temperature the solution is poured on water
  2. extractionthe organic components are extracted with dichloromethane/ethanol
  3. customRecristallisation of the raw product obtained
  4. concentrationafter concentration

Sources & evidence

ORD record
ord-413cec147b324d009e8e038997855d44
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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