Dichloroacetyl chloride → HCID 19826608, compound

HRID 1086139Notes

Reaction equation

HRID 1086139 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][NH:7][CH:8]([CH3:12])[CH2:9][O:10][CH3:11].COC1C=C(C=CC=1OC)CN.COCC(=O)C.[OH-].[Na+].[Cl:38][CH:39]([Cl:43])[C:40](Cl)=[O:41]>C1(C)C=CC=CC=1.C1(C)C=CC=CC=1.CCCCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][N:7]([CH:8]([CH3:12])[CH2:9][O:10][CH3:11])[C:40](=[O:41])[CH:39]([Cl:43])[Cl:38]

Participants

9

Reactant 5

HCID 6593Dichloroacetyl chloride2×HCID 14798Sodium HydroxideHCID 22172MethoxyacetoneHCID 79832VeratrylamineHCID 2851434(3,4-dimethoxybenzyl)(2-methoxy-1-methylethyl)amine

Product 1

HCID 19826608HCID 19826608, compoundYield 61.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 22340243HCID 22340243, compoundSolvent

Procedure

A solution consisting of 23.8 g of N-(3,4-dimethoxybenzyl)-N-(2-methoxy-1-methylethyl)amine (prepared by condensing 3,4-dimethoxybenzylamine and methoxy acetone and hydrogenating the condensation product), 80 ml of toluene, and 20 ml of water in which 4 g of solid sodium hydroxide were dissolved is prepared and cooled down to -10° to -15°. Another solution of 14.7 g of dichloroacetylchloride in 10 ml of toluene is then added dropwise thereto while stirring. The mixture is stirred for one hour after all the dichloro-acetylchloride is added and the poured into 1 l of ice-water. The organic layer that formed was then extracted with ether, washed with diluted hydrochloric acid and twice with water, dried and concentrated. The residue crystallises spontaneously and yields 30.9 g of raw product melting at 62°-63°. After recrystalliation from a toluene/pentane mixture one obtained 21.3 g of pure title product melting at 75°-76°.

Workup

  1. dissolutionwere dissolved
  2. customis prepared
  3. temperaturecooled down to -10° to -15°
  4. additionis added
  5. customThe organic layer that formed
  6. extractionwas then extracted with ether
  7. washwashed with diluted hydrochloric acid and twice with water
  8. customdried
  9. concentrationconcentrated
  10. customThe residue crystallises spontaneously
  11. customyields 30.9 g of raw product melting at 62°-63°

Sources & evidence

ORD record
ord-e73846c0ef554dd7989223ff330cb59a
Source dataset
uspto-grants-1991_07
Patent number
US05028256

Reaction notes

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