Acetic Acid → 2-[4-[(4-Chlorophenyl)cyanomethyl]3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid

HRID 1165843Notes

Reaction equation

HRID 1165843 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:27]#[N:28])[C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])C(C#N)=[N:16]3)=[CH:11][C:10]=2[O:25][CH3:26])=[CH:4][CH:3]=1.Cl.[C:30]([OH:33])(=[O:32])[CH3:31]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:27]#[N:28])[C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[C:31]([C:30]([OH:33])=[O:32])=[N:16]3)=[CH:11][C:10]=2[O:25][CH3:26])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 230351972-[4-[(4-Chlorophenyl)cyanomethyl]-3-methoxyphenyl]2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile

Product 1

HCID 230351952-[4-[(4-Chlorophenyl)cyanomethyl]3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid

Procedure

A mixture of 4 parts of 2-[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carbonitrile, 24 parts of concentrated hydrochloric acid and 40 parts of acetic acid is stirred and refluxed for 3 hours. The reaction mixture is evaporated in vacuo and the residue is stirred in water. The product is extracted with a mixture of trichloromethane and methanol (90:10 by volume). The extract is dried, filtered and evaporated, yielding 2-[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]-2,3,4,5-tetrahydro-3,5-dioxo-1,2,4-triazine-6-carboxylic acid.

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture is evaporated in vacuo
  3. stirringthe residue is stirred in water
  4. extractionThe product is extracted with a mixture of trichloromethane and methanol (90:10 by volume)
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d3739c3d1e5b4f7b8c010c1d03a9449e
Source dataset
uspto-grants-1990_03
Patent number
US04912106

Reaction notes

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