p-Toluidine → [(4-Methylphenyl)carbamoyl]sulfamyl chloride

HRID 556305Notes

Reaction equation

HRID 556305 reaction equation
[Cl:1][S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1>C(OCC)C>[CH3:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[NH:5][S:2]([Cl:1])(=[O:4])=[O:3])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7813p-ToluidineHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 55279229[(4-Methylphenyl)carbamoyl]sulfamyl chlorideYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

This compound was prepared according to J. Med. Chem. 1996, 39, 1243-1252. Briefly, a solution of chlorosulfonylisocyanate (1.62 g, 11.5 mmol, 1 eq.) was diluted in dry diethylether and the resulting solution was cooled at −50° C.<T<−40° C. To this solution, p-toluidine (1.23 g, 11.5 mmol, 1 eq.) was added. The solution was stirred at −35° C. for 10′ and a suspension was obtained. The solid was filtered and washed with diethyl ether. Yield 80%, 2.3 g.

Workup

  1. customThis compound was prepared
  2. customwas obtained
  3. filtrationThe solid was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-109c2c1f01d84a11a7d26b62fd73f0f8
Source dataset
uspto-grants-2011_11
Patent number
US08058262B2

Reaction notes

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