Dimethylformamide → HCID 20342541, compound

HRID 2050330Notes

Reaction equation

HRID 2050330 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9](Cl)[C:8](Cl)=[N:7]2)([O-:3])=[O:2].C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.CN(C)[CH:25]=[O:26]>O>[N+:1]([C:4]1[CH:13]=[CH:12][C:11]2[N:10]=[C:9]3[N:18]4[CH2:19][CH2:20][CH2:22][CH:21]4[CH2:25][O:26][C:8]3=[N:7][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 6890902,3-Dichloro-6-nitroquinoxaline

Product 1

HCID 20342541HCID 20342541, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 24.4 g. portion of 6-nitro-2,3-dichloroquinoxaline is added in one portion to a mixture of 10.2 g. of L-2-pyrrolidinomethanol, 40 ml. of triethylamine and 400 ml. of dimethylformamide which has been cooled to -5° C. in an ice bath. The mixture is stirred in the ice bath for 5 minutes, then at room temperature for 2 hours, finally on a steam bath overnight. A 500 ml. portion of water is added in increments. The mixture is cooled to room temperature and the solid is collected by filtration, washed with water, then hexane and dried. This solid is boiled in 300 ml. of dichloromethane and then filtered. The filtrate is passed through Magnesol® and hexane is added giving a solid. The solid is recrystallized from ethyl acetate giving the desired product, m.p. 234°-237° C.

Workup

  1. customovernight
  2. filtrationthe solid is collected by filtration
  3. washwashed with water
  4. dry with materialhexane and dried
  5. filtrationof dichloromethane and then filtered
  6. additionis added
  7. customgiving a solid
  8. customThe solid is recrystallized from ethyl acetate giving the desired product, m.p. 234°-237° C.

Sources & evidence

ORD record
ord-b20d90107a8849ff990063f8f1b1b7af
Source dataset
uspto-grants-1980_04
Patent number
US04200748

Reaction notes

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