Chloroform → HCID 19593922, compound

HRID 612324Notes

Reaction equation

HRID 612324 reaction equation
[S:1](Cl)(Cl)=O.OCCCNC(=O)CS[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1.C([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])C.[CH:27]([Cl:30])(Cl)Cl>>[Cl:30][CH2:27][CH2:26][CH2:25][NH:22][C:23](=[S:1])[CH2:24][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1

Participants

5

Reactant 4

HCID 6212Chloroform2×HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 19593896HCID 19593896, compound

Product 1

HCID 19593922HCID 19593922, compoundYield 25%

Procedure

Thionyl chloride (3.5 g, 30 mmol) in chloroform (20 cm3) was added dropwise to a solution of N-(3-hydroxypropyl)-(tetrahydropyran-2-ylthio)acetamide 35 (5.5 g, 23.5 mmol) and triethylamine (3.5 g, 35 mmol) in chloroform (50 cm3), and the mixture stirred at room temperature for 48 h. The resulting solution was extracted with water (2×35 cm3), dried (MgSO4), filtered, and volatile components removed under reduced pressure to give the N-(3-chloropropyl)-tetrahydropyran-2-ylthioacetamide (1.5 g, 25%) as an oil. This material was sufficiently pure to be used without further purification.

Workup

  1. extractionThe resulting solution was extracted with water (2×35 cm3)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customvolatile components removed under reduced pressure

Sources & evidence

ORD record
ord-942ecf86801e4aa8bfba6223dbe729bf
Source dataset
uspto-grants-1999_12
Patent number
US06004531

Reaction notes

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