Triethylamine → 2-[(2-Chloro-5-isopropenyl-phenyl)-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide

HRID 1674664Notes

Reaction equation

HRID 1674664 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:12]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)(=[O:23])=[O:22])[CH2:13][C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15].CCN(CC)CC.CS(Cl)(=O)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[CH2:9])=[CH:4][C:3]=1[N:12]([S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)(=[O:22])=[O:23])[CH2:13][C:14]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 575113202-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide

Product 1

HCID 247600902-[(2-Chloro-5-isopropenyl-phenyl)-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamideYield 38.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[[2-chloro-5-(1-hydroxy-1-methyl-ethyl)-phenyl]-(3,4-dimethoxy-benzenesulfonyl)-amino]-N,N-diethyl-acetamide (0.527 g, 1 mmol) in DCM (10 mL) was added at 0° C. NEt3 (0.88 mL, 6 eq) and DMAP (7 mg). Methane sulfonylchloride (0.123 mL, 1.5 eq) was added and the mixture warmed to RT and stirred for 6 h. The mixture was partitioned between DCM and water. The aqueous phase was once more extracted with DCM and the combined organic layers dried over MgSO4 and concentrated. The residue was purified by chromatography on SiO2 (hex/EA 1:1, EA, EA/MeOH 9:1) to give the title compound as a colourless solid (0.186 g, 37%). Unreacted starting material (0.29 g, 55%) was also recovered.

Workup

  1. customThe mixture was partitioned between DCM and water
  2. extractionThe aqueous phase was once more extracted with DCM
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on SiO2 (hex/EA 1:1, EA, EA/MeOH 9:1)

Sources & evidence

ORD record
ord-9b6ee56759ab45e397ef138defd67e09
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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