Methylamine → HCID 53630783, compound

HRID 2382661Notes

Reaction equation

HRID 2382661 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([OH:13])(=O)=[O:11].S(Cl)(Cl)(=O)=O.S(Cl)(Cl)=O.[CH3:23][NH2:24]>ClC(Cl)C.O>[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([NH:24][CH3:23])(=[O:13])=[O:11]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 69362-Amino-5-chloro-4-methylbenzenesulfonic acidHCID 24386Thionyl ChlorideHCID 24648Sulfuryl chloride

Product 1

HCID 53630783HCID 53630783, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-amino-5-chloro-4-methyl-benzenesulfonic acid (3.0 g, 1.35 mmol) in dichloroethane (10 mL) is added sulfuryl chloride (4.4 mL, 3.83 mmol) and stirred at 60° C. After one hour, thionyl chloride (1.3 mL) is added and the mixture is further stirred at 100° C. for 7.0 hours. The mixture is poured into iced water and extracted with ether three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. 1H-NMR (δ, ppm): 2.35 (s, 3H), 6.68 (s, 1H), 7.75 (s, 1H). This substituted sulfonyl chloride is reacted with a suitable amine. On reaction e.g. with methylamine, 2-amino-5-chloro-4,N-dimethylbenzenesulfonamide is formed.

Workup

  1. stirringthe mixture is further stirred at 100° C. for 7.0 hours
  2. extractionextracted with ether three times
  3. washThe organic layer is washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThis substituted sulfonyl chloride is reacted with a suitable amine

Sources & evidence

ORD record
ord-45ed8bc8e6304859a6c77c6e62918eee
Source dataset
uspto-grants-2012_09
Patent number
US08263590B2

Reaction notes

Loading…