Acetic Acid → HCID 178429211, compound

HRID 2309369Notes

Reaction equation

HRID 2309369 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].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH:20]=O.C(O)(=O)C>C(O)C>[CH3:13][C:5]1([CH3:14])[C:4]2[C:8](=[CH:9][C:10]3[NH:11][C:20]([C:16]4[S:15][CH:19]=[CH:18][CH:17]=4)=[N:1][C:2]=3[CH:3]=2)[NH:7][C:6]1=[O:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73642-ThiophenecarboxaldehydeHCID 135892372H-Indol-2-one, 5,6-diamino-1,3-dihydro-3,3-dimethyl-

Product 1

HCID 178429211HCID 178429211, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3.8 g. (20 mmol) 5,6-diamino-3,3-dimethylindolin-2-one, 2.25 g. (20 mmol) thiophene-2-aldehyde and 4 ml. glacial acetic acid in 40 ml. ethanol is heated under reflux for 1 hour and then further boiled for 1 hour, while passing through air. The reaction mixture is then distilled to dryness and the residue stirred up with ethyl acetate and filtered off with suction. The crystallisate obtained is recrystallised from acetone. Yield: 1.7 g. (30% of theory); m.p. 332°-336° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThe reaction mixture is then distilled to dryness
  3. filtrationfiltered off with suction
  4. customThe crystallisate obtained
  5. customis recrystallised from acetone

Sources & evidence

ORD record
ord-b623b3f08df74cb1aae4ba8130bb4f78
Source dataset
uspto-grants-1987_09
Patent number
US04695567

Reaction notes

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