3-Formyl-2-methylindole → 1,4-Benzenediamine, N4-ethyl-N4-(2-methoxyethyl)-2-methyl-, 4-methylbenzenesulfonate (1:2)

HRID 355624Notes

Reaction equation

HRID 355624 reaction equation
C[S:2](N[C:6]1[CH:16]=[CH:15][C:9]([C:10](CC#N)=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].C[C:18]1[NH:19][C:20]2[C:25]([C:26]=1C=O)=[CH:24][CH:23]=[CH:22][CH:21]=2.[C:29]([O-:32])(=[O:31])C.[NH4+:33]>C(O)(=O)C>[C:25]1([CH3:26])[CH:24]=[CH:23][C:22]([S:2]([OH:4])(=[O:31])=[O:3])=[CH:21][CH:20]=1.[C:25]1([CH3:26])[CH:24]=[CH:23][C:22]([S:2]([OH:4])(=[O:31])=[O:3])=[CH:21][CH:20]=1.[NH2:33][C:8]1[CH:7]=[CH:6][C:16]([N:19]([CH2:18][CH3:26])[CH2:20][CH2:25][O:32][CH3:29])=[CH:15][C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 731663-Formyl-2-methylindoleHCID 517165Ammonium AcetateHCID 14646930Methanesulfonamide, N-[4-(2-cyanoacetyl)phenyl]-

Product 1

HCID 212259861,4-Benzenediamine, N4-ethyl-N4-(2-methoxyethyl)-2-methyl-, 4-methylbenzenesulfonate (1:2)

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-methanesulfonamidobenzoylacetonitrile (10 g, 42 mmol), 2-methylindole-3-carboxaldehyde (7.3 g, 46 mmol) and ammonium acetate (1 g, 12.6 mmol) in 80 mL acetic acid was heated to reflux and held 3 h. The reaction was then cooled to 25° C., and the precipitated dye collected by filtration and washed with acetic acid. The crude dye was slurried in hot acetic acid for 30 min then collected by filtration and dried. Isolated 13 g (82%) of Dye 5. All analytical data were consistent with the structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationthe precipitated dye collected by filtration
  4. washwashed with acetic acid
  5. waitThe crude dye was slurried in hot acetic acid for 30 min
  6. filtrationthen collected by filtration
  7. customdried
  8. customIsolated 13 g (82%) of Dye 5

Sources & evidence

ORD record
ord-ea3282adb61343a3b44e2bd875926466
Source dataset
uspto-grants-1998_11
Patent number
US05834173

Reaction notes

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