Hydrochloric Acid → HCID 67046796, compound

HRID 1438388Notes

Reaction equation

HRID 1438388 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].N1C=C[CH:12]=[CH:11][CH:10]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].[Cl-].[Cl-].[Cl-].[Al+3].C(Cl)(=[O:26])C.Cl>C(Cl)Cl.C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[CH:8]=[C:7]([C:10](=[O:26])[CH2:11][CH3:12])[CH:6]=[CH:5][C:3]=1[NH:4][S:16]([CH3:15])(=[O:18])=[O:17]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 7242O-ToluidineHCID 31297Methanesulfonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67046796HCID 67046796, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylaniline (2.2 g, 20 mmol, purchased from TCl) in pyridine (1.7 ml. 1.7 g, 21.4 mmol) and DCM (85 ml), methanesulfonyl chloride (1.6 ml, 2.3 g, 20 mmol) was added dropwise over 10 minutes at 0° C. The reaction mixture was stirred at room temperature for 1 hour. After cooling to 0° C., aluminum trichloride (6.8 g, 51 mmol) was added to the reaction mixture carefully. Then acetyl chloride (1.9 g, 20 mmol) was added dropwise over 15 minutes. The reaction mixture was diluted with toluene (25 ml) and poured into 2 M HCl aqueous solution (500 ml) with stirring at 0° C. The precipitates were filtered,washed with water and dried in vacuo to afford the title compound (2.1 g, 43%) as yellow solids.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringwith stirring at 0° C
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a2aa513e62a8444a9972517ce52a7586
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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