HCID 22125755, compound → HCID 18990339, compound

HRID 1974700Notes

Reaction equation

HRID 1974700 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 1

HCID 22125755HCID 22125755, compound

Product 1

HCID 18990339HCID 18990339, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
20 °C

Procedure

A solution containing 0.5 g of the product obtained in Example 24 in 2.5 ml of thionyl chloride was refluxed for 10 min. The excess of thionyl chloride was 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 was washed with 1N 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 chloride was evaporated in vacuo
  3. dissolutionthe residue dissolved in 25 ml of dichloromethane
  4. additionTo this solution 0.47 g of isopropylamine was added
  5. washDichloromethane phase was washed with 1N hydrochloric acid
  6. customevaporated in vacuo
  7. customThe residue was crystallized from toluene

Sources & evidence

ORD record
ord-07d184844bce4f8291ccb5ab97359f86
Source dataset
uspto-grants-1994_02
Patent number
US05283352

Reaction notes

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