Water → 4-(3-Ethylthioureido)benzenesulfonic acid

HRID 1809959Notes

Reaction equation

HRID 1809959 reaction equation
Cl[S:2]([OH:4])=[O:3].[CH2:5]([NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[S:9])[CH3:6].[OH2:17]>CCOC(C)=O>[CH2:5]([NH:7][C:8](=[S:9])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:2]([OH:4])(=[O:17])=[O:3])=[CH:13][CH:12]=1)[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 422778Chlorosulfanic acidHCID 2063659Thiourea, N-ethyl-N'-phenyl-

Product 1

HCID 583498474-(3-Ethylthioureido)benzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of chlorosulfanic acid (3 mL) is cooled to 0° C. and 1-ethyl-3-phenylthiourea (360 mg, 2.0 mmol) is then added over a period of 5 minutes and the resulting mixture is stirred at 0° C. for 2 hour followed by addition of water (10 mL) which results in the formation of a precipitate. EtOAc is added to dissolve the precipitate and the mixture is extracted (5×15 mL). The combined organic layers are concentrated and dissolved in a mixture of dioxane and water (12 mL, 1:1). The resulted mixture is heated to 80° C. for 2 hr. and concentrated to provide 4-(3-ethylthioureido)benzenesulfonic acid (1-4) as an off white solid. HPLC-MS calculated for C9H12N2O3S2 (M+H+) 261.0. found 261.0.

Workup

  1. customresults in the formation of a precipitate
  2. dissolutionto dissolve the precipitate
  3. extractionthe mixture is extracted (5×15 mL)
  4. concentrationThe combined organic layers are concentrated
  5. dissolutiondissolved in a mixture of dioxane and water (12 mL, 1:1)
  6. temperatureThe resulted mixture is heated to 80° C. for 2 hr
  7. concentrationand concentrated

Sources & evidence

ORD record
ord-91be14c900b24835bfb3d333de3e6dbc
Source dataset
uspto-grants-2013_01
Patent number
US08362050B2

Reaction notes

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