Pyridine → 4-Acetamidophenyl sulfamate

HRID 327689Notes

Reaction equation

HRID 327689 reaction equation
[S:1](=[O:11])(=[O:10])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:2].[C:12]([NH:15]C1C=CC(O)=CC=1)(=[O:14])[CH3:13].N1C=CC=CC=1>O1CCOCC1>[NH2:2][S:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:15][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1983AcetaminophenHCID 11030308Phenylsulfamate

Product 1

HCID 110316784-Acetamidophenyl sulfamateYield 43.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

A reaction flask was charged with 43.8 g (0.252 mole) of sulfamic acid, phenyl ester; 12.6 g (0.084 mole) of 4-acetamidophenol, 9 ml of pyridine and 150 ml p-dioxane. The solution was heated at 75° C. for 18 hours. The solution was concentrated to a brown oil. The oil was portioned between 100 ml methylene chloride and 100 ml of 1.0 N sodium bicarbonate. The mixture was refrigerated overnight then filtered to collect 15.8 g of white solid. 1H NMR spectrum indicated pure product but contaminated with sodium bicarbonate. The solid was added to 100 ml H2O and the mixture stirred for one hour. The solid was collected and dried to give 8.4 g of solid, mp 180°-181° C.

Workup

  1. concentrationThe solution was concentrated to a brown oil
  2. filtrationthen filtered
  3. customto collect 15.8 g of white solid
  4. additionThe solid was added to 100 ml H2O
  5. customThe solid was collected
  6. customdried

Sources & evidence

ORD record
ord-4d0dcdd11d284f8dbedcbf5f4a12d8e1
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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