Trichloroacetyl chloride → HCID 20397151, compound

HRID 462430Notes

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

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. 3. N-(3,5-Dichloro-4-formamidophenyl)-trichloroacetamide may be prepared from N-(4-amino-3,5-dichlorophenyl)-trichloroacetamide as follows:

Workup

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

Sources & evidence

ORD record: ord-9d694b8c8b7548d197ba8ce207c34050
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04515800

Reaction notes

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