(Chlorothio)formyl chloride → 2H-1,3,4-Oxathiazol-2-one

HRID 2358454Notes

Reaction equation

HRID 2358454 reaction equation
O1CCC(C[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[Cl:17])[C:10]([C:18]([NH2:20])=[O:19])=[CH:9]2)CC1.Cl[C:22]([S:24]Cl)=[O:23]>O1CCCC1>[O:23]1[CH2:22][CH2:9][CH:10]([CH2:18][C:13]2[CH:12]=[C:11]3[C:16](=[C:15]([Cl:17])[CH:14]=2)[NH:8][CH:9]=[CH:10]3)[CH2:11][CH2:12]1.[O:19]1[CH:18]=[N:20][S:24][C:22]1=[O:23]

Participants

5

Reactant 2

HCID 75990(Chlorothio)formyl chlorideHCID 68538635HCID 68538635, compound

Product 2

HCID 221149662H-1,3,4-Oxathiazol-2-oneYield 111.1%HCID 86611814HCID 86611814, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(tetrahydropyran-4-yl)methyl-7-chloro-1H-indole-3-carboxylic acid amide (8.0 g, 27.0 mmol) in tetrahydrofuran (100 ml) was added chlorocarbonylsulfenyl chloride (4.7 ml, 55.0 mmol) and the reaction mixture was heated at reflux for 3 h and allowed to cool. The precipitate was filtered off and dried to give 5-(1-tetrahydropyran-4-yl) methyl-7-chloro-1H-indole)-[1,3,4]-oxathiazol-2-one (5.3 g, 15.0 mmol) as a white solid. The filtrate was concentrated in vacuo, and the resulting solid was washed with 5% ethylacetate in n-heptane then dried to leave 7-chloro-3-([1,3,4]-oxathiazol-2-on-5-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole (2.6 g, 7.0 mmol) as a pink solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-e3b921f736d3494185aa5ef06139ae3c
Source dataset
uspto-grants-2010_07
Patent number
US07763732B2

Reaction notes

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