Water → HCID 21515664, compound

HRID 1284154Notes

Reaction equation

HRID 1284154 reaction equation
O.[C:2]1([C:8]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)O)=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]1[O:27][C:26]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=2[O:19]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl.C1(C)C(C)=CC=CC=1>[C:2]1([C:8]2[NH:23][C:22]3[C:24]([C:10]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:25][C:26]2[O:27][CH2:18][O:19][C:20]=2[CH:21]=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8400BenzoinHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 21515664HCID 21515664, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7237O-XyleneSolvent

Procedure

To a flask equipped with a stirrer and Dean-Stark water separator are charged 53g. of benzoin, 51g. of 3,4-methylenedioxyaniline, 2.5g. of p-toluenesulfonic acid and 300 ml. of xylene. The mixture is stirred and refluxed for 10 hours. After cooling to room temperature 1500 ml of chloroform are added and the organic layer is washed two times with 150 ml. of 10%, sulfuric acid. The organic layer is treated with charcoal, filtered and concentrated in vacuo to ca. 500 ml. On standing there is obtained 2,3-diphenyl- 5,6-methylenedioxyindole, m.p. 187°-188°C.

Workup

  1. customTo a flask equipped with a stirrer
  2. temperaturerefluxed for 10 hours
  3. additionare added
  4. washthe organic layer is washed two times with 150 ml
  5. additionThe organic layer is treated with charcoal
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to ca. 500 ml

Sources & evidence

ORD record
ord-37ac049b785c4c54a780a765909d3178
Source dataset
uspto-grants-1976_08
Patent number
US03978086

Reaction notes

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