Chloroacetamide → HCID 2515442, compound

HRID 1105715Notes

Reaction equation

HRID 1105715 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].[OH-].[K+].Cl[CH2:15][C:16]([NH2:18])=[O:17].O1CCOCCOCCOCCOCCOC=C1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([O:6][CH2:15][C:16]([NH2:18])=[O:17])=[O:5]

Participants

6

Reactant 4

HCID 6580ChloroacetamideHCID 97962,6-Difluorobenzoic acidHCID 14797Potassium HydroxideHCID 54139501HCID 54139501, compound

Product 1

HCID 2515442HCID 2515442, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

This compound was prepared in the manner of Example I, using 10.0 grams (0.063 mole) of 2,6-difluorobenzoic acid, 4.2 grams (0.063 mole) of potassium hydroxide, 5.9 grams (0.063 mole) of 2-chloroacetamide, and 1.7 grams of 1,4,7,10,13,16-hexaoxacyclooctadecene in 250 ml of dry toluene. The crude product was recrystallized once with ethyl acetate, then with ethyl acetate-hexane, using decolorizing carbon. The yield was 5.2 grams of (aminocarbonyl)methyl 2,6-difluorobenzoate; mp 108.5°-110°. The ir and the nmr spectra were consistent with the proposed structure.

Workup

  1. customThis compound was prepared in the manner of Example I
  2. customThe crude product was recrystallized once with ethyl acetate

Sources & evidence

ORD record
ord-2d3148d98e924a3ab62818078e9efe52
Source dataset
uspto-grants-1982_01
Patent number
US04309566

Reaction notes

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