Hydrochloric Acid → Benzenesulfonamide, 4-amino-N-(thioxo(tricyclo(3.3.1.1(sup 3,7))dec-1-ylamino)methyl)-

HRID 1577576Notes

Reaction equation

HRID 1577576 reaction equation
[C:1]12([NH:11][C:12]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(=O)C)=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH-].[Na+].Cl.NC1C=CC=CC=1S(NC(N)=S)(=O)=O>O>[C:1]12([NH:11][C:12]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3007731HCID 3007731, compoundHCID 20571169HCID 20571169, compound

Product 1

HCID 3007732Benzenesulfonamide, 4-amino-N-(thioxo(tricyclo(3.3.1.1(sup 3,7))dec-1-ylamino)methyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 28.25 g. (0.070 mol) of 1-adamantyl-3-(4-acetamidophenylsulfonyl)thiourea and 28 g. (0.70 mol) of sodium hydroxide in 500 ml. of water was refluxed for 1 hour. On cooling, the pH of the mixture was adjusted to 1 by dropwise addition of 6 N hydrochloric acid and the precipitate was recrystallized from methanol-water to give 20.8 g. (83%) of the (aminophenylsulfonyl)thiourea, m.p. 176°-179°.

Workup

  1. additionA suspension of 28.25 g
  2. temperatureOn cooling
  3. customthe precipitate was recrystallized from methanol-water
  4. customto give 20.8 g

Sources & evidence

ORD record
ord-7be9142177984139a4ed3e88e2608775
Source dataset
uspto-grants-1981_09
Patent number
US04288454

Reaction notes

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