HCID 10036749, compound → HCID 19813424, compound

HRID 345040Notes

Reaction equation

HRID 345040 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1.Cl[CH2:17][C:18]1[O:19][C:20]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:21]=2[C:22]=1[CH3:23]>C(O)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][CH:10]=1)[CH2:17][C:18]1[O:19][C:20]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:21]=2[C:22]=1[CH3:23]

Participants

4

Reactant 2

HCID 10036749HCID 10036749, compoundHCID 19813434HCID 19813434, compound

Product 1

HCID 19813424HCID 19813424, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Methyl-4-methanesulphonamidophenethylamine (1.66 g, 7.3 mmole) and 2-chloromethyl-3-methyl-5-nitrobenzofuran (see Preparation 7B - 0.82 g, 3.6 mmole) were heated at reflux temperature in ethanol (20 ml) for 3 hours. The solvent was then evaporated and the residue was purified by column chromatography on silica eluting with methylene chloride/hexane (4:1) followed by methylene chloride containing methanol (0% up to 5%). The product-containing fractions were combined and evaporated, and the residue was recrystallised from ethanol to give the title compound, yield 1.52 g, m.p. 124°-124.5°.

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was purified by column chromatography on silica eluting with methylene chloride/hexane (4:1)
  3. additioncontaining methanol (0% up to 5%)
  4. customevaporated
  5. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-f1c4461425974b4e99959fac0a2f5ce1
Source dataset
uspto-grants-1991_10
Patent number
US05055473

Reaction notes

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