Chloroacetyl chloride → HCID 86061066, compound

HRID 1263176Notes

Reaction equation

HRID 1263176 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([CH3:17])=[CH:15][CH3:16])[C:8]=1[NH2:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([CH3:17])=[CH:15][CH3:16])[C:8]=1[NH:9][C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471Triethylamine2×HCID 54006107HCID 54006107, compound

Product 1

HCID 86061066HCID 86061066, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.007 mole of chloroacetyl chloride was added dropwise to a mixture of 0.007 moles of 2-methyl-6-(1-methylprop-1-enyl)-aniline and 0.008 moles (1.15 ml) of triethylamine in methylene chloride at about but below 20° C. The mixture was then refluxed and then allowed to stand overnight at room temperature. The mixture was then again refluxed and allowed to stand for two days (over the weekend) at room temperature. Thin layer chromatographic (plate) analysis showed the presence of a small amount of starting material. An additional 0.55 ml of triethylamine and 0.3 ml of chloroacetyl chloride was added and the mixture again refluxed and allowed to stand overnight at room temperature. The mixture was then washed with aqueous sodium bicarbonate, dried and evaporated affording 1.7 g of the title compound as a slightly crystallized oil (m.p. 71°-74° C.).

Workup

  1. temperatureThe mixture was then refluxed
  2. temperatureThe mixture was then again refluxed
  3. waitto stand for two days
  4. customat room temperature
  5. temperaturethe mixture again refluxed
  6. waitto stand overnight at room temperature
  7. washThe mixture was then washed with aqueous sodium bicarbonate
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-7bf394036d764abba5a15f4644786e2f
Source dataset
uspto-grants-1984_06
Patent number
US04456471

Reaction notes

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