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

HRID 973807
Notes
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Reaction equation

HRID 973807 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=1)[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])#[N:2].[Cl:15][C:16]([Cl:20])([Cl:19])[C:17]#[N:18].[Br-].[Al+3].[Br-].[Br-].[ClH:25]>ClCCl>[Cl:15][C:16]([Cl:20])([Cl:19])[C:17]1[N:18]=[C:17]([C:16]([Cl:19])([Cl:15])[Cl:25])[N:18]=[C:1]([C:3]2[CH:4]=[C:5]([CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])[N:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11011TrichloroacetonitrileHCID 166749BromhydrolHCID 53396017Methyl 3-(3-cyanophenyl)prop-2-enoate

Product 1

HCID 57080114Methyl 3-(4,6-bis(trichloromethyl)-s-triazin-2-yl)cinnamate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

Methyl 3-cyanocinnamate (42 pw) is added to a mixture of trichloroacetonitrile (194.4 pw) and aluminum bromide (7.2 pw) in the absence of moisture and at about 25° C. Hydrogen chloride is then introduced over a period of 3 hours with stirring, while keeping the temperature constant. Stirring is discontinued, and the mixture is allowed to react further overnight. In this step, too, a constant temperature of 25° C. is maintained. The solidified mixture is dissolved in 800 pw of dichloromethane, washed with water, and the organic phase is dried over sodium sulfate. Evaporation of the solvent gives a white residue, which is recrystallized from methanol or benzene.

Workup

  1. stirringStirring
  2. customto react further overnight
  3. washwashed with water
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgives a white residue, which
  7. customis recrystallized from methanol or benzene

Sources & evidence

ORD record
ord-e7d0a1bdac0446449d77f36e1bb57a4b
Source dataset
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05064959

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes