Hydrochloric Acid → 4-Acetyl-2-chlorobenzenesulfonamide

HRID 1098752Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.[CH2:13]([O:15]C=C[Sn](CCCC)(CCCC)CCCC)[CH3:14].Cl.C([O-])(O)=O.[Na+]>C(#N)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the product obtained in step 1 (1.0 g, 3.70 mmol) in ACN (8 ml) was added CuI (35 mg, 185 μmol), PdCl2(PPh3)2 (389 mg, 554 μmol) and 1-(ethoxyvinyl)tributyl-stannane (2.5 ml, 2.60 g, 7.39 mmol). The mixture was heated for 30 min at 100° C. using microwaves. After cooling, the reaction mixture was acidified with 1 N HCl (4 ml) and stirred for 20 min. The reaction mixture was adjusted to pH=7 using NaHCO3 and extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane (1:1) gave the desired product (650 mg, 75%).

Workup

temperatureAfter cooling
extractionextracted with AcOEt
washThe organic phase was washed with brine
dry with materialdried over Na2SO4
customevaporated
customPurification of the crude product by silica gel chromatography

Sources & evidence

ORD record: ord-dbe3a4443df94318b8c7124ee4bb2785
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143242B2

Reaction notes

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