1,1'-Carbonyldiimidazole → HCID 178481587, compound

HRID 568817Notes

Reaction equation

HRID 568817 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([CH3:25])([CH3:24])[C:19](=[O:23])[NH:20]2)=[CH:16][C:15]=1[NH:26][CH3:27]>O1CCOCC1>[CH3:27][N:26]1[C:15]2[CH:16]=[C:17]3[C:18]([CH3:24])([CH3:25])[C:19](=[O:23])[NH:20][C:21]3=[CH:22][C:14]=2[N:13]=[C:1]1[OH:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 20149363HCID 20149363, compound

Product 1

HCID 178481587HCID 178481587, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9.8 g. 1,1'-Carbonyldiimidazole are added to 6.1 g. 6-amino-5-methylamino-3,3-dimethylindolin-2-one in 250 ml. dioxan and the reaction mixture is heated under reflux for 2 hours. The solution is evaporated to dryness in a vacuum and the reddish oil remaining behind is boiled under reflux for 2 hours with 20% aqueous hydrochloric acid. The mixture is cooled to ambient temperature and neutralised with aqueous ammonia solution, while cooling with ice. The precipitate is filtered off with suction and recrystallised from methanol. There are obtained 2.0 g. of the title compound; m.p. 364°-367° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solution is evaporated to dryness in a vacuum
  3. temperatureunder reflux for 2 hours with 20% aqueous hydrochloric acid
  4. temperaturewhile cooling with ice
  5. filtrationThe precipitate is filtered off with suction
  6. customrecrystallised from methanol
  7. customThere are obtained 2.0 g

Sources & evidence

ORD record
ord-3e8e6fb5dd4d4929af88bfbbb0efdc03
Source dataset
uspto-grants-1988_03
Patent number
US04730003

Reaction notes

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