Tributylamine → 1,2-Benzisothiazole, 3-chloro-5-nitro-

HRID 277375

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][NH:10][C:9](=O)[C:8]=2[CH:13]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O.C(N(CCCC)CCCC)CCC>C(Cl)Cl>[Cl:16][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[S:11][N:10]=1

Participants

Conditions

Temperature: 109 °C

Procedure

A mixture of 5-nitro-1,2-benzisothiazol-3(2H)-one (10.0 g, 0.0510 mol), phosphorus oxychloride (40.0 mL, 0.429 mol) and tributylamine (12.0 mL, 0.050 mol) is heated at 103-115° C. for six hours, stirred at room temperature overnight, and poured into an ice-water mixture. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with water and saturated sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a gum. Column chromatography of the gum using silica gel and methylene chloride gives the title product as an orange-yellow solid which is identified by NMR spectral analysis.

Workup

extractionThe resultant aqueous mixture is extracted with methylene chloride
washThe combined organic extracts are washed sequentially with water and saturated sodium hydrogen carbonate solution
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain a gum

Sources & evidence

ORD record: ord-b97e097d6d624ba4aaf28e75807e741e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355796B1

Linked notes

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