Chloroform → HCID 19593922, compound

HRID 1584541Notes

Reaction equation

HRID 1584541 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 (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-f808e17b2bd44ea6816b8a804bc0ffbd
Source dataset
uspto-grants-1999_08
Patent number
US05932707

Reaction notes

Loading…