p-Toluenesulfonic acid → HCID 178429208, compound

HRID 1193575Notes

Reaction equation

HRID 1193575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[C:5]2([CH3:14])[CH3:13].[N:15]1([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH:19]=[CH:18][N:17]=[CH:16]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:24]([C:23]4[CH:22]=[CH:21][C:20]([N:15]5[CH:19]=[CH:18][N:17]=[CH:16]5)=[CH:27][CH:26]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429208HCID 178429208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g. (10.4 mmol) 5,6-diamino-3,3-dimethyl-indolin-2-one, 1.8 g. (10.4 mmol) 4-(1H-imidazol-1-yl)-benzaldehyde, 0.2 g. (1 mmol) p-toluenesulphonic acid and 120 ml. ethanol were mixed together, heated to the boiling point and air passed therethrough for 3 hours. After concentration and acidification with ethanolic hydrochloric acid, the crystallisate obtained was filtered off with suction, suspended in water and neutralised with an aqueous solution of ammonia. The residue obtained was recrystallised from methanol. There was obtained 1.0 g. (28% of theory) of the title compound; m.p. 300° C.

Workup

  1. temperatureheated to the boiling point and air
  2. concentrationAfter concentration and acidification with ethanolic hydrochloric acid
  3. customthe crystallisate obtained
  4. filtrationwas filtered off with suction
  5. customThe residue obtained
  6. customwas recrystallised from methanol
  7. customThere was obtained 1.0 g

Sources & evidence

ORD record
ord-f6b4fd2520814924888ce70c253851f0
Source dataset
uspto-grants-1989_03
Patent number
US04810801

Reaction notes

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