Hydrochloric Acid → HCID 131713132, compound

HRID 647229Notes

Reaction equation

HRID 647229 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl>N1C=CC=CC=1>[S:16]([O:8][C:7]1[C:2]([NH:1][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])=[CH:3][C:4]([CH3:9])=[CH:5][CH:6]=1)([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72642-Amino-4-methylphenolHCID 73974-Toluenesulfonyl chloride2×

Product 1

HCID 131713132HCID 131713132, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 2-amino-p-cresol (12.3 g, 0.10 mol) in 125 ml of pyridine was added p-toluenesulfonyl chloride (38.1 g, 0.20 mol) in one portion. Stirring was continued overnight at ambient temperature. TLC now indicated no starting material, but there were two products. Another 7.6 g (20 percent excess) of p-toluenesulfonyl chloride was added and stirring continued for 6 hours. The reaction was poured into excess hydrochloric acid and stirred until completely solidified. The tan solid precipitate was filtered, washed with water and nearly dried. The damp filter cake was dissolved in one liter of boiling ethanol and let stand overnight at ambient temperature. Yield 33.0 g (76 percent) of crystals. NMR was consistent for the product.

Workup

  1. stirringstirring
  2. waitcontinued for 6 hours
  3. stirringstirred
  4. filtrationThe tan solid precipitate was filtered
  5. washwashed with water
  6. customnearly dried
  7. dissolutionThe damp filter cake was dissolved in one liter of boiling ethanol
  8. waitlet stand overnight at ambient temperature

Sources & evidence

ORD record
ord-bcff623d597f468b8880a7f1a643612c
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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