Sulfuric Acid → HCID 118093608, compound

HRID 1520094Notes

Reaction equation

HRID 1520094 reaction equation
S(=O)(=O)(O)[OH:2].N[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:9][CH:8]=1.N([O-])=O.[Na+]>O>[OH:2][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 27781314-Amino-N-methylbenzenemethanesulfonamideHCID 23668193Sodium Nitrite

Product 1

HCID 118093608HCID 118093608, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Add sulfuric acid (2.5 mL, 44.9 mmol) to a suspension of 1-(4-aminophenyl)-N-methyl-methanesulfonamide (7.5 g, 37.5 mmol) in water (56.2 mL) and chill the reaction mixture to 0° C. Slowly, drop wise add a solution of sodium nitrite (2.8 g; 41.2 mmol) in water (37.5 mL) to this slurry. Stir the resulting mixture at 0° C. for 20 m, then remove the ice bath and heat the reaction at 100° C. Cool the mixture to room temperature. Quench the reaction with an excess of water and extract with EtOAc. Combine the EtOAc extracts, wash the extracts with brine; dry over MgSO4; filter; and concentrate the filtrate under reduced pressure to yield the title compound as an orange solid (6.2 g, 66%). MS (m/z): 219 (M+H2O).

Workup

  1. customremove the ice bath
  2. temperatureheat
  3. customthe reaction at 100° C
  4. temperatureCool the mixture to room temperature
  5. customQuench
  6. customthe reaction with an excess of water
  7. extractionextract with EtOAc
  8. washwash the extracts with brine
  9. dry with materialdry over MgSO4
  10. filtrationfilter
  11. concentrationand concentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-d128f66d239a46f68d6c71ffade4e76c
Source dataset
uspto-grants-2015_07
Patent number
US09073901B2

Reaction notes

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