Water → 3-cyano-N-methylbenzene-1-sulfonamide

HRID 219675Notes

Reaction equation

HRID 219675 reaction equation
[CH3:1][NH2:2].O.[C:4]([C:6]1[CH:7]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1)#[N:5]>C(Cl)Cl>[C:4]([C:6]1[CH:7]=[C:8]([S:12]([NH:2][CH3:1])(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1)#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 28013603-Cyanobenzene-1-sulfonyl chloride

Product 1

HCID 175619913-cyano-N-methylbenzene-1-sulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A flask containing DCM (90 mL) and methylamine in water (40 wt %, 7.5 mmol) is chilled in an ice water bath with magnetic stirring. 3-Cyano-benzenesulfonyl chloride (5 g, 2.49 mmol) is added along with DCM (10 mL) to wash down the sides of the flask. After 30 min, concentrated HCl in water is added at 0° C., until the reaction is acidic (pH<4). Water (50 mL) is added and DCM is removed in vacuo. The residue is filtered to afford 3-cyano-N-methyl-benzenesulfonamide as a solid (99%). MS: 195 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.76 (d, 3H), 4.48 (broad-s, N—H), 7.7 (t, 1H), 7.9 (d, 1H), 8.13 (d, 1H), 8.19 (s, 1H).

Workup

  1. temperatureis chilled in an ice water bath with magnetic stirring
  2. washto wash down the sides of the flask
  3. additionconcentrated HCl in water is added at 0° C., until the reaction
  4. additionWater (50 mL) is added
  5. customDCM is removed in vacuo
  6. filtrationThe residue is filtered

Sources & evidence

ORD record
ord-962010c3fa1b4a5dae2ab374dafabd33
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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