Chloroacetyl chloride → HCID 18630274, compound

HRID 1263175Notes

Reaction equation

HRID 1263175 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(N(CC)CC)C.[CH3:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:24][CH2:25][CH3:26])([CH3:23])[CH3:22])[C:15]=1[NH2:16]>C(Cl)Cl>[CH3:13][C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:24][CH2:25][CH3:26])([CH3:23])[CH3:22])[C:15]=1[NH:16][C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 8471Triethylamine2×HCID 20454928HCID 20454928, compound

Product 1

HCID 18630274HCID 18630274, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example 1.45 g (1.03 ml) of chloroacetyl chloride was added dropwise to a solution containing 1.44 g (2 ml) of triethylamine and 0.0129 mole of 2-methyl-6-(1-ethoxy-1-methylethyl)aniline in methylene chloride at about but below 20° C. The mixture was then refluxed and then allowed to stand overnight at room temperature. Another 0.51 ml of chloroacetyl chloride and 1 ml of triethylamine was then added dropwise. The mixture was then again refluxed and allowed to stand overnight at room temperature. The mixture was then washed with saturated aqueous sodium bicarbonate, dried and evaporated affording the title compound as a brown oil.

Workup

  1. temperatureThe mixture was then refluxed
  2. temperatureThe mixture was then again refluxed
  3. waitto stand overnight at room temperature
  4. washThe mixture was then washed with saturated aqueous sodium bicarbonate
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1bd151cc3ecb4fb8b7adb54220ddcfa7
Source dataset
uspto-grants-1984_06
Patent number
US04456471

Reaction notes

Loading…