Toluene → HCID 21806293, compound

HRID 1742804Notes

Reaction equation

HRID 1742804 reaction equation
[CH:1]([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[S:7])([CH3:3])[CH3:2].S(Cl)(Cl)=[O:14].[C:17]1([CH3:23])C=CC=C[CH:18]=1>>[CH:1]([C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH:17]1[CH2:23][O:14][CH2:18]1)=[S:7])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 178440042HCID 178440042, compound

Product 1

HCID 21806293HCID 21806293, compound

Conditions

Temperature
80 °C

Procedure

A mixture of 19.7 g of 2-isopropylthionicotinic acid prepared according to Example 1 and 22 ml of thionyl chloride in 100 ml of absolute toluene is stirred for 3 hours at 80° C. When evolution of gas has ceased, the reaction mixture is filtered and the mother liquor is concentrated to dryness under vacuum. The residual crude product (20.8 g of 2-isopropylthionicotinyl chloride as a yellow oil) is dissolved in 70 ml of absolute toluene and treated slowly at a temperature of 20°-25° C. with a mixture of 8.8 g of oxetan-3-ol and 8.5 ml pyridine dissolved in 20 ml of toluene. After stirring for 12 hours at a temperature of 20°-25° C., 100 ml of ice-water and 200 ml of diethyl ether are added, the organic phase is separated, and the aqueous phase is extracted with 2×100 ml of diethyl ether. The combined organic phase is dried and concentrated to give 27.4 g of oxetan-3-yl 2-isopropylthionicotinate in the form of a pale yellow oil. Purification by distillation at a bath temperature of 145°-150° C., 4×10-2 bar) gives 19.7 g of an oil.

Workup

  1. customprepared
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe mother liquor is concentrated to dryness under vacuum
  4. dissolutionThe residual crude product (20.8 g of 2-isopropylthionicotinyl chloride as a yellow oil) is dissolved in 70 ml of absolute toluene
  5. additiontreated slowly at a temperature of 20°-25° C. with a mixture of 8.8 g of oxetan-3-ol and 8.5 ml pyridine
  6. dissolutiondissolved in 20 ml of toluene
  7. stirringAfter stirring for 12 hours at a temperature of 20°-25° C., 100 ml of ice-water and 200 ml of diethyl ether
  8. additionare added
  9. customthe organic phase is separated
  10. extractionthe aqueous phase is extracted with 2×100 ml of diethyl ether
  11. customThe combined organic phase is dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-cfaab56aa18b406da70a373df70d1e54
Source dataset
uspto-grants-1994_08
Patent number
US05342823

Reaction notes

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