Water → HCID 18630232, compound

HRID 1263178Notes

Reaction equation

N1C=CC=CC=1.[CH3:7][C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:19])([O:17][CH3:18])[CH3:16])[C:9]=1[NH2:10].[Cl:20][CH2:21][C:22](Cl)=[O:23].O>C(Cl)Cl>[CH3:7][C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([CH3:19])([O:17][CH3:18])[CH3:16])[C:9]=1[NH:10][C:22](=[O:23])[CH2:21][Cl:20]

Participants

Conditions

Temperature: 25 °C

Procedure

216.46 g (2.74 mols) of pyridine was slowly added to a solution containing 467.5 g (2.61 mols) of 2-methyl-6-(1-methyl-1-methoxyethyl)-aniline in 2.74 liters of methylene chloride at room temperature (about 18°-25° C.). 309.62 g (2.74 mols) of chloroacetyl chloride was added dropwise over a 20-minute period. The temperature of the mixture was maintained at about, or less than, 25° C. during this addition. The mixture was then stirred at about 18° C. for about 1 hour and then mixed with two liters of water. The methylene chloride phase was then separated treated with aqueous 5 wt. % hydrochloric acid until slightly acidic and then washed with water and dried over magnesium sulfate. The mixture was then evaporated to dryness affording a brownish solid which was then washed with a 10% isopropanol:90% hexane mixture affording 484 g of the title compound.

Workup

additionduring this addition
customThe methylene chloride phase was then separated
additiontreated with aqueous 5 wt. % hydrochloric acid until slightly acidic and
washthen washed with water
dry with materialdried over magnesium sulfate
customThe mixture was then evaporated to dryness
customaffording a brownish solid which
washwas then washed with a 10% isopropanol

Sources & evidence

ORD record: ord-bfd26d634c3447c2b4bf6f8579b11c2d
Source dataset: uspto-grants-1984_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04456471

Reaction notes

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