Hydrochloric Acid → HCID 86738123, compound

HRID 1155556Notes

Reaction equation

HRID 1155556 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([N+:18]([O-])=O)[CH2:14][CH:13]=1)[C:6](=[O:10])[CH:7]([Cl:9])[Cl:8].Cl.[OH-].[NH4+]>CC(C)=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([NH2:18])[CH2:16][CH:17]=1)[C:6](=[O:10])[CH:7]([Cl:8])[Cl:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86738124HCID 86738124, compound

Product 1

HCID 86738123HCID 86738123, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

23 ml of a 15% solution of TiCl3 was added to 1.6 g of N-(β-methoxy-ethyl)-N-[4-phenoxy-(4'-nitro)-benzyl]-dichloroacetamide, in 30 ml of acetone; the pH was then adjusted to 3 with 23% HCl. The resulting mixture was stirred at room temperature for 24 hours and then, with cooling, brought to pH 9 with concentrated ammonium hydroxide. The resulting precipitate was removed by filtration and washed with water. The filtrated was extracted several times with chloroform. The combined organic extract was then dried on Na2SO4 and evaporated to dryness to give 1.2 g of N-(β-methoxy-ethyl)-N-[4-phenoxy-(4'-amino)-benzyl]-dichloroacetamide, m.p. 100°-102° C.

Workup

  1. temperaturewith cooling
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with water
  4. extractionThe filtrated was extracted several times with chloroform
  5. extractionThe combined organic extract
  6. customwas then dried on Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c25f56a7f97e43b0b90719e540698b39
Source dataset
uspto-grants-1981_11
Patent number
US04302472

Reaction notes

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