3-Hydroxyacetanilide → HCID 19108671, compound

HRID 1613402Notes

Reaction equation

HRID 1613402 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[S:12](Cl)(=[O:15])(=[O:14])[NH2:13].ClS(N=C=O)(=O)=O>O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([O:11][S:12](=[O:15])(=[O:14])[NH2:13])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 121243-HydroxyacetanilideHCID 24499Chlorosulfamic acidHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 19108671HCID 19108671, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

By the same method described for Example 53, the title compound was prepared from m-acetamidophenol (12.10 g, 0.08 m), reacting with the sulfamoyl chloride generated from water and chlorosulfonyl isocyanate. The crude product contained desired product and starting material. The product was isolated by chromatography on 100 g silica gel, eluted first with 7:3 methylene chloride/acetonitrile and then increasing the proportion of acetonitrile in the eluting solvent. The main fraction was evaporated and triturated with isopropyl alcohol/isopropyl ether to give 4 g of white solid, recrystallized from acetonitrile/isopropyl ether, and dried in vacuum at 60° C. overnight to give 3.73 g of solid, mp 148°-149° C.

Workup

  1. customThe product was isolated by chromatography on 100 g silica gel
  2. washeluted first with 7:3 methylene chloride/acetonitrile
  3. temperatureincreasing the proportion of acetonitrile in the eluting solvent
  4. customThe main fraction was evaporated
  5. customtriturated with isopropyl alcohol/isopropyl ether

Sources & evidence

ORD record
ord-d942ca7ec32e47788db7e6fcebf621fd
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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