Thionyl Chloride → HCID 131725153, compound

HRID 496599Notes

Reaction equation

HRID 496599 reaction equation
[CH:1]1([C:7]([NH:9][CH:10]([OH:15])[C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[CH:1]1([C:7]([NH:9][C:10]([Cl:18])([OH:15])[C:11]([Cl:13])([Cl:14])[Cl:12])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20829800HCID 20829800, compound

Product 1

HCID 131725153HCID 131725153, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

Next, cyclohexyl-N-(1,2,2,2-tetrachloro-1-hydroxyethyl) carboxamide 4 was synthesized as follows. A mixture of compound 3 (8.0 g, 20 mmol) and thionyl chloride (4.7 mL, 63.8 mmol, 2.2 equivalents) in dry benzene (30 mL) was heated at 80° C. in an oil bath. The initial suspension eventually became a clear solution (reaction time depends on the amount of starting materials, in this example it took about 5 hours). The mixture was stirred for an additional 30 minutes. The solvents were removed by evaporation under reduced pressure (rotovapor), and the resulting white solid was washed with hexanes and filtered, to produce the desired product 4 (7.0 g). NMR (1H, CDCl3): δ 6.59 (d, 1H), 6.30 (d, 1H), 2.19 (m, 1H), 1.89-1.19 (m, 10H).

Workup

  1. customNext, cyclohexyl-N-(1,2,2,2-tetrachloro-1-hydroxyethyl) carboxamide 4 was synthesized
  2. customreaction time
  3. customThe solvents were removed by evaporation under reduced pressure (rotovapor)
  4. washthe resulting white solid was washed with hexanes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-611ed66ad0304182a3ea67acaeb7e1a2
Source dataset
uspto-grants-2005_09
Patent number
US06946474B2

Reaction notes

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