Trichloroacetyl chloride → HCID 20397151, compound

HRID 462765Notes

Reaction equation

HRID 462765 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[NH2:10].C(N(CC)CC)C.[Cl:18][C:19]([Cl:24])([Cl:23])[C:20](Cl)=[O:21]>C(Cl)Cl>[NH2:10][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([NH:8][C:20](=[O:21])[C:19]([Cl:24])([Cl:23])[Cl:18])=[CH:5][C:4]=1[Cl:9]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 118602,6-Dichloro-1,4-benzenediamine

Product 1

HCID 20397151HCID 20397151, compoundYield 113.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

2,6-Dichloro-1,4-benzenediamine (225 g., 1.27 mol) is suspended in methylene chloride (1.3 liters) containing triethylamine (245 mL, 1.7 mol). After the mixture is cooled to 5° C., trichloroacetylchloride (169 mL, 1.5 mol, Aldrich Chemical Co.) is added dropwise with stirring at a rate to maintain 5° C. Upon complete addition, the stirred reaction is allowed to reach room temperature. After 24 hours the mixture is filtered and the collected solid is washed with methylene chloride (700 mL). The filtrate is evaporated to a small volume. A solid is collected and washed with methylene chloride (250 mL) to yield 465 grams of N-(4-amino-3,5-dichlorophenyl)-trichloroacetamide. The product exhibits a mass spectral analysis of m/e+· 320 for C8H5Cl5N2O.

Workup

  1. temperatureto maintain 5° C
  2. additionUpon complete addition
  3. customthe stirred reaction
  4. customto reach room temperature
  5. filtrationAfter 24 hours the mixture is filtered
  6. washthe collected solid is washed with methylene chloride (700 mL)
  7. customThe filtrate is evaporated to a small volume
  8. customA solid is collected
  9. washwashed with methylene chloride (250 mL)

Sources & evidence

ORD record
ord-8714a4cfa7d042ef9ac1484bcc34307e
Source dataset
uspto-grants-1985_05
Patent number
US04517199

Reaction notes

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