Dichloromethane → HCID 19939966, compound

HRID 36080Notes

Reaction equation

HRID 36080 reaction equation
C(O[C:4]([C:8]1[C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH3:22])([CH3:21])[CH:9]=1)=[N:5][C:6]#[N:7])C.[CH:23]1([NH2:26])[CH2:25][CH2:24]1.ClCCl.CCOC(C)=O>CCCCCC>[C:6]([NH:5][C:4]([C:8]1[C:13]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH3:21])([CH3:22])[CH:9]=1)=[N:26][CH:23]1[CH2:25][CH2:24]1)#[N:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 69828CyclopropylamineHCID 15234750HCID 15234750, compound

Product 1

HCID 19939966HCID 19939966, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 98 mg of N-cyano -6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboximidic acid ethyl ester, 30 mg of cyclopropylamine, and 1 ml of dichloromethane was stirred at room temperature for 1.5 hours. The reaction mixture was subjected to silica gel column chromatography (AcOEt:n-hexane=l:l) and then recrystallization from a mixture of acetone and n-hexane to obtain 30 mg of N-cyano-N'-cyclopropyl-6-nitro-2,2-dimethyl-2H-1-benzopyran -4-carboxamidine represented by formula shown below.

Workup

  1. customrecrystallization
  2. additionfrom a mixture of acetone and n-hexane

Sources & evidence

ORD record
ord-233c6b08c8c74cc8b43a33f85898d23e
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

Loading…