Thionyl Chloride → HCID 13712584, compound

HRID 1757946Notes

Reaction equation

HRID 1757946 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]([CH2:16]O)[C:7](=[O:18])[CH2:6][O:5]1)(=[O:3])[CH3:2].S(Cl)([Cl:21])=O>>[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]([CH2:16][Cl:21])[C:7](=[O:18])[CH2:6][O:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13712582HCID 13712582, compound

Product 1

HCID 13712584HCID 13712584, compoundYield 53%

Conditions

Temperature
0 °C

Procedure

0.5 g. (2 mmoles) of 2-acetyl-3-phenyl-4-hydroxymethyltetrahydro-1,2,4-oxadiazin-5-one are refluxed in 3 ml. of thionyl chloride for one hour. The solution is evaporated to dryness under reduced pressure. The residue is triturated with diethyl ether cooled to 0° C. and the product is filtered off and is subsequently recrystallized from a mixture of 2 ml. of chloroform and 6 ml. of n-hexane. 0.28 g. (53%) of 2-acetyl-3-phenyl-4-chloromethyl-tetrahydro-1,2,4-oxadiazin-5-one are obtained, melting at 171° to 172° C.; RfA =0.7.

Workup

  1. customThe solution is evaporated to dryness under reduced pressure
  2. customThe residue is triturated with diethyl ether
  3. filtrationthe product is filtered off
  4. customis subsequently recrystallized from a mixture of 2 ml

Sources & evidence

ORD record
ord-6d4e0fbb561e494cb0ab98bd3656b7ee
Source dataset
uspto-grants-1983_02
Patent number
US04371534

Reaction notes

Loading…