Dimethylformamide dimethyl acetal → 4-[[4-[(2,6-Dichlorophenyl)methyl]-6-[[(dimethylamino)methylene]amino]-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 1062556Notes

Reaction equation

HRID 1062556 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]2[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:16])[N:5]=[C:4]([NH:17][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]=1.CO[CH:28](OC)[N:29]([CH3:31])[CH3:30]>>[Cl:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[CH2:8][C:6]1[N:7]=[C:2]([N:1]=[CH:28][N:29]([CH3:31])[CH3:30])[N:3]=[C:4]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=2)[N:5]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4863624-[[4-Amino-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

Product 1

HCID 4864454-[[4-[(2,6-Dichlorophenyl)methyl]-6-[[(dimethylamino)methylene]amino]-1,3,5-triazin-2-yl]amino]benzonitrile

Procedure

Compound (1) (0.0016 mol) and 1,1-dimethoxy-N,N-dimethylmethanamine (21 ml) were combined and stirred vigorously at ambient temperature for 8 hours. The reaction mixture was filtered and the collected solid was washed with ether (Fraction A). Additional compound was obtained by concentration of the filtrate (Fraction B). Fractions A and B were combined and recrystallized from ethanol, yielding 0.15 g of 4-[[4-[(2,6-dichlorophenyl)methyl]-6-[[(dimethylamino)methylene]amino]-1,3,5-triazin-2-yl]amino]benzonitrile (compound 62).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe collected solid was washed with ether (Fraction A)
  3. customAdditional compound was obtained by concentration of the filtrate (Fraction B)
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-43310d9af149485eb19d892a65275cd0
Source dataset
uspto-grants-2005_11
Patent number
US06962916B2

Reaction notes

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