N-Methylaniline → HCID 18365400, compound

HRID 380559Notes

Reaction equation

HRID 380559 reaction equation
ClC1C=CC(OC)=CC=1.ClS(O)(=O)=O.[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:26][CH3:27])=[C:20]([S:22](Cl)(=[O:24])=[O:23])[CH:21]=1.[CH3:28][NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([O:26][CH3:27])=[C:20]([S:22]([N:29]([CH3:28])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:24])=[O:23])[CH:21]=1

Participants

5

Reactant 4

HCID 7515N-MethylanilineHCID 121674-ChloroanisoleHCID 24638Chlorosulfonic acidHCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

Product 1

HCID 18365400HCID 18365400, compound

Conditions

Temperature
15 °C

Procedure

The liquid is cooled to 15° C. in an ice-water bath, and 27 mL of 4-chloroanisole (95 w/w %) is carefully added to chlorosulfonic acid. The mixture is stirred between additions and the temperature of the mixture is kept below 50° C. When the addition is complete, the mixture is refluxed on a steam bath for 2 hours. A homogeneous, viscous liquid is formed. The reaction mixture is then carefully poured into a 250 mL beaker of ice water. A white, solid mass of 5-chloro-2-methoxybenzenesulfonyl chloride is precipitated, filtered and dried (m.p. 88-89° C.). The 5-chloro-2-methoxybenzenesulfonyl chloride (15.7 g, ˜0.07 mole) is added to 7.0 g (˜0.07 mole) of N-methyl aniline by the procedure for making sulfonanilides as described previously. A light brown oil, 5-chloro-2-methoxy-N-methylbenzenesulfonanilide, (16 g, 80t yield) is obtained. 1H NMR (deuterioacetone): δ 6.3-7.9 (m, 8 ArH), 3.8 (s, 3H, OCH3), 3.2 (s, 3H, N—CH3); ms:m/z 311 (M+).

Workup

  1. customis kept below 50° C
  2. additionWhen the addition
  3. temperaturethe mixture is refluxed on a steam bath for 2 hours
  4. customA homogeneous, viscous liquid is formed
  5. customA white, solid mass of 5-chloro-2-methoxybenzenesulfonyl chloride is precipitated
  6. filtrationfiltered
  7. customdried (m.p. 88-89° C.)

Sources & evidence

ORD record
ord-9abc6ed6c869449dbb96f244b093721f
Source dataset
uspto-grants-2001_10
Patent number
US06303630B1

Reaction notes

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