Thionyl Chloride → HCID 18990339, compound

HRID 1757635Notes

Reaction equation

HRID 1757635 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=O)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].S(Cl)(Cl)=O>>[CH:6]([NH:9][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]([OH:8])=[C:2]([OH:1])[CH:3]=1)([CH3:7])[CH3:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22125755HCID 22125755, compound

Product 1

HCID 18990339HCID 18990339, compound

Conditions

Temperature
20 °C

Procedure

A solution containing 0.5 g of the product obtained in Example 24 in 2.5 mlof thionyl chloride was refluxed for 10 min. The excess of thionyl chloridewas evaporated in vacuo and the residue dissolved in 25 ml of dichloromethane. To this solution 0.47 g of isopropylamine was added and the mixture was Stirred for 1 h at 20° C. Dichloromethane phase waswashed with 1 N hydrochloric acid and evaporated in vacuo. The residue was crystallized from toluene. Yield 0.44 g (75%), m.p. 113°-115° C.

Workup

  1. temperaturewas refluxed for 10 min
  2. customThe excess of thionyl chloridewas evaporated in vacuo
  3. dissolutionthe residue dissolved in 25 ml of dichloromethane
  4. additionTo this solution 0.47 g of isopropylamine was added
  5. customevaporated in vacuo
  6. customThe residue was crystallized from toluene

Sources & evidence

ORD record
ord-391c2d5321f14d76afe86a2b4ce08611
Source dataset
uspto-grants-1995_08
Patent number
US05446194

Reaction notes

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