Sulfuryl chloride → HCID 68550970, compound

HRID 1868013Notes

Reaction equation

HRID 1868013 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:14]1([S:24](Cl)(=[O:26])=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.S(Cl)(Cl)(=O)=O.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][N:11]([S:24]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)(=[O:26])=[O:25])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24648Sulfuryl chlorideHCID 665601-Naphthalenesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 114129441-(3-Chloropyridin-2-yl)piperazine

Product 1

HCID 68550970HCID 68550970, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of 1-(3-chloropyridin-2-yl)piperazine (316 mg, 1.6 mmol) with naphthalene-1-sulfonyl chloride (362.7 mg, 1.6 mmol) was carried out according to a similar procedure described for example 2A (Except sulfonyl chloride was added before diisopropylethylamine) using anhydrous dichloromethane (3 mL) as solvent and diisopropylethylamine (1.4 mL, 8.0 mmol) as base. 1-(3-chloropyridin-2-yl)-4-(1-naphthylsulfonyl)piperazine was obtained in 70.0% yield (434.0 mg) as white solid.

Sources & evidence

ORD record
ord-f666420a3119496f975a222c3b9371cc
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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