Pyridine → 1-naphthyl N-(N'-benzenesulfonyl-N'-methylaminosulfinyl)-N-methylcarbamate

HRID 1660520Notes

Reaction equation

HRID 1660520 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.[S:22](Cl)(Cl)=[O:23].[CH3:26][NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29]>O1CCCC1>[C:31]1([S:28]([N:27]([CH3:26])[S:22]([N:2]([CH3:1])[C:3](=[O:15])[O:4][C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)=[O:23])(=[O:30])=[O:29])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6129CarbarylHCID 24386Thionyl ChlorideHCID 78858N-Methylbenzenesulfonamide

Product 1

HCID 129599981-naphthyl N-(N'-benzenesulfonyl-N'-methylaminosulfinyl)-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-naphthyl methylcarbamate (4.0 g, 0.02 mol) in 20 ml dry tetrahydrofuran was added pyridine (2.0 g, 0.025 mol) followed by thionyl chloride (2.5 g, 0.021 mol). The mixture was stirred at room temperature for 4 hours. Pyridine (2 g, 0.025 mol) was added and followed by 3.5 g (0.02 mol) N-methylbenzenesulfonamide and the mixture was stirred at room temperature overnight.

Workup

  1. stirringthe mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-e64338fb37b14dd495bd51008c144bd1
Source dataset
uspto-grants-1981_12
Patent number
US04308274

Reaction notes

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