2-Aminobenzenesulfonic acid → HCID 10803520, compound

HRID 2293618Notes

Reaction equation

HRID 2293618 reaction equation
[CH:1]1[CH:6]=[C:5]([NH2:7])[C:4]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:3][CH:2]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:14]>O>[NH2:7][C:5]1[CH:6]=[CH:1][C:2]([C:13]([CH3:14])([CH3:12])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:3][C:4]=1[S:8]([OH:11])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 69262-Aminobenzenesulfonic acidHCID 7407Alpha-Methylstyrene2×

Product 1

HCID 10803520HCID 10803520, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Orthanilic acid (1 kg) and α-methylstyrene (683g) are mixed with stirring in water (4.631) and heated at reflux for 8 hours. Further portions (2×148 g) of α-methylstyrene are added over 30 minute periods with refluxing for 6 hours. The mixture is filtered at 85° C. and the recovered solid product washed with boiling water and then with ethanol and dried in a vacuum oven. The product is stirred with ether (150ml), filtered off and dried. Recrystallisation from 50% aqueous ethanol affords 1-amino-4-(α,α-dimethylbenzyl)benzene-2-sulphonic acid, m.p. 263°-265° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. temperaturewith refluxing for 6 hours
  4. filtrationThe mixture is filtered at 85° C.
  5. washthe recovered solid product washed with boiling water
  6. dry with materialwith ethanol and dried in a vacuum oven
  7. filtrationfiltered off
  8. customdried
  9. customRecrystallisation from 50% aqueous ethanol

Sources & evidence

ORD record
ord-a8eb7953cf514573a172d6be8e34b874
Source dataset
uspto-grants-1997_11
Patent number
US05686564

Reaction notes

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