Chloroacetyl chloride → HCID 57952168, compound

HRID 603344Notes

Reaction equation

HRID 603344 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]([C:21](=[O:22])[CH2:20][Cl:19])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 57952164HCID 57952164, compound

Product 1

HCID 57952168HCID 57952168, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

N-(2′,4′Dichloro-6′-methylphenyl)-4-ethylaniline (4.83 g as a mixture with the byproduct N,N-di-(4-ethylphenyl)-2′,4′-dichloro-6′-methylaniline) is dissolved in 4.18 g of chloro acetylchlorid and heated to 100° C. for 1.5 h. The mixture is cooled, diluted with toluene (50 ml) and extracted with aqu. sodium bicarbonate. The organic phase is evaporated to dryness and chromatographed on silica (75 g) eluting with toluene to afford unreacted N,N-di-(4-ethylphenyl)-2′,4′-dichloro-6′-methylaniline and N-(2′,4-dichloro-6′-methylphenyl)-N-chloroacetyl-4-ethylaniline (2.95 g). A crystallised sample melts at 83-84° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with aqu
  3. customThe organic phase is evaporated to dryness
  4. customchromatographed on silica (75 g)
  5. washeluting with toluene

Sources & evidence

ORD record
ord-0f7d2cc1ce57474d8094eb1386f50879
Source dataset
uspto-grants-2011_03
Patent number
US07906677B2

Reaction notes

Loading…