4-(Dimethylamino)Benzaldehyde → 2-(4-Dimethylaminostyryl)-3-methylbenzotellurazolium Trifluoromethanesulfonate

HRID 2352059Notes

Reaction equation

HRID 2352059 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH3:9][C:10]1[Te:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[N+:14]=1[CH3:15].[CH3:20][N:21]([CH3:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1>C(O)C.N1CCCCC1>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH3:20][N:21]([CH3:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[CH:9][C:10]2[Te:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[N+:14]=2[CH3:15])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 139311742,3-Dimethylbenzotellurazolium Trifluoromethanesulfonate

Product 1

HCID 867434572-(4-Dimethylaminostyryl)-3-methylbenzotellurazolium Trifluoromethanesulfonate

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

2,3-Dimethylbenzotellurazolium trifluoromethanesulfonate (Example 30) (0.80 g, 0.002 mole) and 4-dimethylaminobenzaldehyde (0.30 g, 0.002 mole) were heated together in ethanol (about 30 ml), with one drop of piperidine present, to boiling and maintained at boiling for ten minutes. An intense red color developed. The dye separated as crystals on cooling. After overnight chilling they were isolated by filtration and recrystallized from ethanol, using diethyl ether to aid in reprecipitation. Yield 0.21 g (19% of theory).

Workup

  1. temperaturemaintained
  2. waitat boiling for ten minutes
  3. customThe dye separated as crystals
  4. temperatureon cooling
  5. temperatureAfter overnight chilling they
  6. customwere isolated by filtration
  7. customrecrystallized from ethanol
  8. customto aid in reprecipitation

Sources & evidence

ORD record
ord-02fe101da0074ede83b67ee82db98c70
Source dataset
uspto-grants-1989_10
Patent number
US04874866

Reaction notes

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