Chloroacetamide → HCID 23302056, compound

HRID 1952970Notes

Reaction equation

HRID 1952970 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]([NH2:14])[CH2:6]2.C(=O)(O)[O-].[Na+].Cl[CH2:21][C:22]([NH2:24])=[O:23]>C(O)C>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[CH2:6][CH:7]([NH:14][CH2:21][C:22]([NH2:24])=[O:23])[CH2:8]2

Participants

5

Reactant 3

HCID 6580ChloroacetamideHCID 516892Sodium BicarbonateHCID 110416235,6-dimethoxy-2,3-dihydro-1H-inden-2-amine

Product 1

HCID 23302056HCID 23302056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5,6-Dimethoxy-2-indanylamine (0.024 moles, 4.6 g) and sodium bicarbonate (0.026 moles, 2.2 g) are added to a solution of chloroacetamide (0.024 moles, 2.2 g) in absolute ethanol (100 ml) and refluxed for 10 hours. The mixture is filtered at r.t. and the solution is evaporated to dryness. The resulting oil is chromatographed under medium pressure through silica gel (eluent: methylene chloride/methanol=90/10) Yield: 1.95 g (32.7%)--m.p.=135-138° C.

Workup

  1. temperaturerefluxed for 10 hours
  2. filtrationThe mixture is filtered at r.t.
  3. customthe solution is evaporated to dryness
  4. customThe resulting oil is chromatographed under medium pressure through silica gel (eluent: methylene chloride/methanol=90/10) Yield: 1.95 g (32.7%)

Sources & evidence

ORD record
ord-fefa833ab59b44b6bcfbcf18620be3d7
Source dataset
uspto-grants-2000_09
Patent number
US06114391

Reaction notes

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