Dimethylformamide → HCID 20342554, compound

HRID 2050329Notes

Reaction equation

HRID 2050329 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].ClC1C(Cl)=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.CN(C)[CH:22]=[O:23]>O>[CH2:4]1[N:3]2[C:6]3[C:7]([O:23][CH2:22][CH:1]2[CH2:2][CH2:5]1)=[N:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=1[N:17]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 166592,3-Dichloroquinoxaline

Product 1

HCID 20342554HCID 20342554, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.93 ml. of L-2-pyrrolidinomethanol, 20 ml. of triethylamine, 10.0 g. of 2,3-dichloroquinoxaline and 100 ml. of dimethylformamide is heated on a steam bath for 48 hours. A 200 ml. portion of water is added and the mixture is stored in a freezer for 48 hours. The solid is recovered by filtration, dissolved in dichloromethane, passed through Magnesol® and concentrated. The residue is dissolved in 15 ml. of ethyl acetate, stored in a freezer for several days, concentrated to a crystalline residue and washed with ether. These crystals are recrystallized from 5 ml. of ethanol, giving the desired product as yellow crystals, m.p. 121°-123° C., [α]D25 +114° (methanol).

Workup

  1. additionA mixture of 4.93 ml
  2. filtrationThe solid is recovered by filtration
  3. dissolutiondissolved in dichloromethane
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in 15 ml
  6. waitof ethyl acetate, stored in a freezer for several days
  7. concentrationconcentrated to a crystalline residue
  8. washwashed with ether
  9. customThese crystals are recrystallized from 5 ml

Sources & evidence

ORD record
ord-dc88af2e76a34f9ba2037e0df0cdf149
Source dataset
uspto-grants-1980_04
Patent number
US04200748

Reaction notes

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