Benzylamine → 2-Chloro-3-(2,5-dichloro-4-methylthio-phenoxy)-6-nitro-N-benzyl-aniline

HRID 1902594Notes

Reaction equation

[Cl:1][C:2]1[C:7](OC2C=CC=CC=2)=[C:6]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:4][C:3]=1[S:18][C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([CH3:26])=[CH:21][C:20]=1[Cl:27].[CH2:28]([NH2:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCOCC1>[Cl:1][C:2]1[C:3]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[C:22]([CH3:26])=[CH:21][C:20]=2[Cl:27])=[CH:4][CH:5]=[C:6]([N+:15]([O-:17])=[O:16])[C:7]=1[NH:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4.6 gm of 2-chloro-4-nitro-3-phenoxy-1-(2,5-dichloro-4-methylthio-phenoxy)-benzene, 3.0 gm of benzylamine and 10 ml of dioxane was stirred for 6 hours at 40° C. Thereafter, the reaction mixture was allowed to stand overnight and was then evaporated. The residue was taken up in chloroform, and the resulting solution was extracted first with dilute sodium hydroxide and then with water, dried with sodium sulfate and evaporated. The dark brown oil left behind was purified on a silicagel column, yielding 4.2 gm of the thin-layer chromatographically uniform title compound in the form of an orange, viscous oil.

Workup

waitto stand overnight
customwas then evaporated
extractionthe resulting solution was extracted first with dilute sodium hydroxide
dry with materialwith water, dried with sodium sulfate
customevaporated
waitThe dark brown oil left
custombehind was purified on a silicagel column

Sources & evidence

ORD record: ord-7bf46ab9ebb34437b1cb25bcc909c1a5
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04364875

Reaction notes

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