Water → HCID 69736097, compound

HRID 982592Notes

Reaction equation

HRID 982592 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([CH3:10])[CH3:9])[N:5]=[C:4]([NH:12][CH:13]([CH:23]2[CH2:25][CH2:24]2)[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=1.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[N:1][C:2]2[N:7]=[C:6]([C:8]([F:11])([CH3:9])[CH3:10])[N:5]=[C:4]([NH:12][CH:13]([CH:23]3[CH2:24][CH2:25]3)[CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:3]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 77264-ChlorobenzaldehydeHCID 15510116HCID 15510116, compound

Product 1

HCID 69736097HCID 69736097, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.5 g (7.28 mmol) of 2-amino-4-(1-fluoro-1-methylethyl)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazine, 1.08 g (7.70 mmol) of p-chlorobenzaldehyde and 100 mg of p-toluenesulfonic acid in 80 ml of toluene are boiled for 10 hours in a water separator. When cold, all volatile constituents are distilled. The crude product is purified by column chromatography (eluent:toluene/ethyl acetate=85:15). This gives 3.0 g (89% of theory) of 2-(4-chloro-6-benzylideneamino)-4-(1-fluoro-1-methylethyl-)-6-(1-cyclopropyl-4-phenyl-1-butylamino)-1,3,5-triazine as colorless oil.

Workup

  1. distillationWhen cold, all volatile constituents are distilled
  2. customThe crude product is purified by column chromatography (eluent:toluene/ethyl acetate=85:15)

Sources & evidence

ORD record
ord-f88f5904c0424087a2f0785e49d7cbc3
Source dataset
uspto-grants-2005_03
Patent number
US06861389B2

Reaction notes

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