Anisole → HCID 44235279, compound

HRID 873624Notes

Reaction equation

HRID 873624 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[S:15](=[O:18])(=[O:17])[NH2:16].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:22]2[CH:23]=[CH:24][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)=[CH:8][C:7]=1[S:15]([NH2:16])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 44235279HCID 44235279, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, aluminum chloride (1.95 g, 14.6 mmol) is slurried in dichloromethane (50 mL) then 4-chloro-3-sulfamoyl benzoyl chloride is added and allowed to stir at ambient temperature for 30 minutes. Anisole (683 mg, 6.3 mmol) is added in 2 mL methylene chloride. The reaction is allowed to stir at ambient temperature for 18 hours. The reaction mixture is poured over ice-cold 6 N HCl and extracted with dichloromethane to give a colorless oil. Purification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%) yielded a white foam which is crystallized three times from ether to afford the title compound. 1H NMR (MeOD) δ 3.9 (s, 3H), 7.1 (d, 2H, J=8.84 Hz), 7.7-8.0 (m, 4H), 8.4 (d, 1H, J=1.96 Hz). MS (m/z): 326 (M+1). CHN Calc C, 51.62; H, 3.71; N, 4.3. Found C, 51.70; H, 3.76; N, 4.22. M.P. 156-158° C.

Workup

  1. stirringto stir at ambient temperature for 18 hours
  2. extractionextracted with dichloromethane
  3. customto give a colorless oil
  4. customPurification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%)
  5. customyielded a white foam which
  6. customis crystallized three times from ether

Sources & evidence

ORD record
ord-ba69a6378fdd48cf957be7eb1bbf0117
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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