Pyridine → 4-Acetamidophenyl sulfamate

HRID 1493999Notes

Reaction equation

HRID 1493999 reaction equation
[C:1]1([O:7][S:8](=[O:11])(=[O:10])[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([NH:15]C1C=CC(O)=CC=1)(=[O:14])[CH3:13].N1C=CC=CC=1>O1CCOCC1>[C:12]([NH:15][C:4]1[CH:3]=[CH:2][C:1]([O:7][S:8](=[O:10])(=[O:11])[NH2:9])=[CH:6][CH:5]=1)(=[O:14])[CH3:13]

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 partitioned between 100 ml of methylene chloride and 100 ml of 1.0N sodium bicarbonate. The mixture was refrigerated overnight then filtered to collect 15.8 g of white solid. 1H NMR spectrum indicated pure organic 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. customThe oil was partitioned between 100 ml of methylene chloride and 100 ml of 1.0N sodium bicarbonate
  3. filtrationthen filtered
  4. customto collect 15.8 g of white solid
  5. additionThe solid was added to 100 ml H2O
  6. customThe solid was collected
  7. customdried

Sources & evidence

ORD record
ord-c73d50c31d7b4877aec66c99e09fa7cb
Source dataset
uspto-grants-1991_06
Patent number
US05025031

Reaction notes

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