4-(Propan-2-yl)benzene-1-sulfonyl chloride → HCID 67421220, compound

HRID 1518199Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:17][CH:18]=[CH2:19])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH:21]([CH3:23])[CH3:22])=[CH:25][CH:26]=2)(=[O:32])=[O:31])=[CH:12][CH:11]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of allyl-[2-(4-amino-phenyl)ethyl]-carbamic acid tert-butyl ester (1.86 g, 6.74 mmol) in pyridine (25 ml) at 0° C. was added 4-isopropyl-benzenesulfonyl chloride (1.47 g, 6.74 mmol) and the mixture was stirred at 0° C. for 1 h. After concentration in vacuo the residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with water, dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography (n-heptane/ethyl acetate, 2/1) to give the product as a yellow resin (1.35 g, 43.6 mmol).

Workup

concentrationAfter concentration in vacuo the residue
customwas partitioned between ethyl acetate and saturated aqueous NaHCO3
washThe organic layer was washed with water
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent evaporated under reduced pressure
customThe residue was purified by column chromatography (n-heptane/ethyl acetate, 2/1)

Sources & evidence

ORD record: ord-a4b032d319354092b81c56ea492e0e55
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232426B2

Reaction notes

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