Ammonia → HCID 178458848, compound

HRID 35765Notes

Reaction equation

HRID 35765 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([S:16](Cl)(=[O:18])=[O:17])[C:9]=2[CH3:20])[CH2:5][C:4](=[O:21])[C:3]=1[C:22](=[O:25])[CH2:23][CH3:24].Cl.[NH3:27]>>[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[C:10]([S:16](=[O:18])(=[O:17])[NH2:27])[C:9]=2[CH3:20])[CH2:5][C:4](=[O:21])[C:3]=1[C:22](=[O:25])[CH2:23][CH3:24]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 178458849HCID 178458849, compound

Product 1

HCID 178458848HCID 178458848, compoundYield 81%

Conditions

Temperature
20 °C

Procedure

A mixture of 3-hydroxy-5-(2,4,6-trimethyl-3-chlorosulphonylphenyl)-2-propionylcyclohex-2-en-1-one (1.3 g) and aqueous ammonia (50 ml, 25%) was stirred at 20° C. for 1 hour. The mixture was acidified with dilute hydrochloric acid and the product was extracted into dichloromethane (2×100 ml). The organic layer was dried over anhydrous sodium sulphate and the solvent was removed by evaporation under reduced pressure using a rotary evaporator to give 3-hydroxy-5-(2,4,6-trimethyl-3-sulfamoylphenyl)-2-propionylcyclohex-2-en-1-one (1.1 g, 81%) as a pale brown foam. Proton magnetic resonance spectrum (CDCl3 ;δ in ppm): 1.17 (3H, t):2.42 (3H, s); 2.63 (3H, s); 2.72 (3H, s); 2.8-4.0 (7H, m); 4.98 (2H, s); 6.96 (1H, s); 18.27 (1H, s).

Workup

  1. extractionthe product was extracted into dichloromethane (2×100 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. customthe solvent was removed by evaporation under reduced pressure
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-1b54ffc9edf246a9a8ed7a20a4c649df
Source dataset
uspto-grants-1988_08
Patent number
US04767879

Reaction notes

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