Sulfamic Acid → 4-Methyl-3-nitrobenzenesulfonyl chloride

HRID 846301Notes

Reaction equation

HRID 846301 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].[Cl:11][S:12](O)(=[O:14])=[O:13].S(=O)(=O)(O)N>>[N+:1]([C:4]1[CH:9]=[C:8]([S:12]([Cl:11])(=[O:14])=[O:13])[CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 5987Sulfamic AcidHCID 69442-NitrotolueneHCID 24638Chlorosulfonic acid

Product 1

HCID 5606384-Methyl-3-nitrobenzenesulfonyl chloride

Conditions

Temperature
40 °C

Procedure

137.1 g (1.0 mol) of o-nitrotoluene are added dropwise to 535.9 g (4.6 mol) of chlorosulfonic acid and 2 g of sulfamic acid such that the temperature does not exceed 40° C. The mixture is then stirred at 40° C. for 1 hour and slowly heated to 105° C. It is then stirred at 105° C. for 6 hours, cooled and added dropwise to ice water at 0 to 5° C. The precipitated crystals are filtered off with suction and washed with ice water. 236.1 g of 2-nitrotoluene-4-sulfonyl chloride (water content 10.8%), corresponding to 210.6 g (89% of theory), having a melting point of 40° C. are obtained.

Workup

  1. customdoes not exceed 40° C
  2. temperatureslowly heated to 105° C
  3. stirringIt is then stirred at 105° C. for 6 hours
  4. temperaturecooled
  5. filtrationThe precipitated crystals are filtered off with suction
  6. washwashed with ice water
  7. customare obtained

Sources & evidence

ORD record
ord-8a977c20515740ad9993a4aecce97da6
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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