Hydrochloric Acid → Methyl 3-(4,6-bis(trichloromethyl)-s-triazin-2-yl)benzoate

HRID 973805

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].[Cl:13][C:14]([Cl:18])([Cl:17])[C:15]#[N:16].[Br-].[Al+3].[Br-].[Br-].[ClH:23]>>[Cl:13][C:14]([Cl:18])([Cl:17])[C:15]1[N:16]=[C:15]([C:14]([Cl:17])([Cl:13])[Cl:23])[N:16]=[C:1]([C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])[N:2]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 11011Trichloroacetonitrile

HCID 83554Benzoic acid, 3-cyano-, methyl ester

HCID 166749Bromhydrol

Product 1

HCID 14572905Methyl 3-(4,6-bis(trichloromethyl)-s-triazin-2-yl)benzoate

Procedure

Methyl 3-cyanobenzoate (70 pw) are mixed with trichloroacetonitrile (376 pw) and aluminum bromide (13.9 pw) as described in Example 1, step 2, hydrogen chloride gas is added, the mixture is allowed to react and the reaction product is separated. Recrystallization from ethanol gives 160 pw=82% of white crystals of methyl 3-(4,6-bis(trichloromethyl)-s-triazin-2-yl)benzoate. M.p.: 115 to 117° C.

Workup

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customRecrystallization from ethanol

Sources & evidence

ORD record: ord-75d789af17cf41cba765527cdb44a27a
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05064959

Linked notes

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