Hydrochloric Acid → HCID 67047037, compound

HRID 1438387Notes

Reaction equation

HRID 1438387 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH3:9].[CH3:10][S:11](Cl)(=[O:13])=[O:12].[Cl-].[Cl-].[Cl-].[Al+3].[C:19](Cl)(=[O:21])[CH3:20].Cl>N1C=CC=CC=1.C(Cl)Cl.C1(C)C=CC=CC=1>[C:19]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:11]([CH3:10])(=[O:13])=[O:12])=[C:3]([CH2:8][CH3:9])[CH:4]=1)(=[O:21])[CH3:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 113572-EthylanilineHCID 31297Methanesulfonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67047037HCID 67047037, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-1-ethylbenzene (purchased from TCl, 12.1 g, 100 mmol) in pyridine (8.5 mL) and DCM (20 ml), methanesulfonyl chloride (7.74 ml, 11.4 g, 105 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 (33.3 g, 250 mmol) was added to the reaction mixture carefully. Then acetyl chloride (11 ml, 12 g, 150 mmol) was added dropwise over 15 minutes. The reaction mixture was diluted with toluene (50 ml) and poured into 2 M HCl aqueous solution (100 ml) with stirring at 0° C. The precipitates were filtered, washed with water and dried in vacuo to give the title compound (18 g, 75%) as yellow solids.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringwith stirring at 0° C
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2b1e2cc29880440abd7884c38c69c067
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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