(Chlorothio)formyl chloride → HCID 68541084, compound

HRID 1441265Notes

Reaction equation

HRID 1441265 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18]([NH2:20])=[O:19].Cl[C:22]([S:24]Cl)=[O:23]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH:8]=[C:7]2[C:18]1[O:19][C:22](=[O:23])[S:24][N:20]=1

Participants

4

Reactant 2

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

Product 1

HCID 68541084HCID 68541084, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7-chloro-1-(tetrahydropyran-4-yl)methyl-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 7-chloro-3-([1,3,4]-oxathiazol-2-on-5-yl)-1-(tetrahydropyran-4-yl)methyl-1H-indole (5.3 g, 15.0 mmol) as a white solid. The filtrate was concentrated in vacuo, and the resulting solid was washed with 5% ethyl acetate in n-heptane then dried to afford a further batch of 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-8a5614d03f694028af7b8b16c233c155
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

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