Hydrochloric Acid → 4-Chloro-3-(propan-2-yl)benzene-1-sulfonyl chloride

HRID 1898237Notes

Reaction equation

HRID 1898237 reaction equation
[S:1](=[O:3])=[O:2].[Cl:4][C:5]1[CH:10]=[CH:9][C:8](N)=[CH:7][C:6]=1[CH:12]([CH3:14])[CH3:13].N([O-])=O.[Na+].[ClH:19]>C(O)(=O)C.O.[Cu]Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:1]([Cl:19])(=[O:3])=[O:2])=[CH:7][C:6]=1[CH:12]([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 198914954-Chloro-3-isopropylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 582682384-Chloro-3-(propan-2-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Amounts used: 25 mL of acetic acid was saturated with sulfur dioxide, 671 mg of copper(I) chloride, 4.60 g (27.1 mmol) of 4-chloro-3-isopropyl-phenylamine dissolved in a mixture of 4 mL of acetic acid and 9 mL of concentrated hydrochloric acid, 2.3 g of sodium nitrite in 10 mL of water. Flash chromatography on silica using 3-20% ethyl acetate in hexanes afforded 2.18 g of the product as a white solid. LC-MSD spectrum not observed.

Sources & evidence

ORD record
ord-940a65fb470b40a88ecb9a33a29eb5b5
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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