Oxalic Acid → HCID 21409840, compound

HRID 1283561Notes

Reaction equation

HRID 1283561 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:11]([N:13]([CH3:24])[CH2:14][C:15]([CH3:23])([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:12]>C(OCC)(=O)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][C:27]=1[Cl:28])[C:11]([N:13]([CH3:24])[CH2:14][C:15]([CH3:23])([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:12]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 21409836HCID 21409836, compound

Product 1

HCID 21409840HCID 21409840, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of oxalic acid (0.180 g., 2 mmole) in ethyl acetate (5 ml.) was added to a solution of 3,4-dichloro-N-methyl-N-[2-methyl-2-dimethylamino-hexyl]benzamide (0.69 g., 2 mmole) in ethyl acetate (5 ml.) and the solution boiled for two mins.. The solution was allowed to cool, and reduced in volume to ca. 5 ml., when a colourless oil began to separate. On leaving overnight, white crystals appeared, which were filtered, washed with ethyl acetate and dried to afford 3,4-dichloro-N-methyl-N-[2-methyl-2-dimethylamino-hexyl]benzamide oxalate (0.644 g., 76%), m.p. 130°-135°C.

Workup

  1. temperatureto cool
  2. customto separate
  3. customOn leaving overnight
  4. filtrationwhich were filtered
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-e2629d5f22674fdb8cf03ddd0fc0d3b9
Source dataset
uspto-grants-1976_08
Patent number
US03975443

Reaction notes

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