3-Amino-1,2-propanediol → HCID 19778858, compound

HRID 2081902Notes

Reaction equation

HRID 2081902 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1OC)([O-:3])=[O:2].[NH2:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20]>O>[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[NH:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 735613-Amino-1,2-propanediolHCID 2596492,6-Dinitro-4-methylanisole

Product 1

HCID 19778858HCID 19778858, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.05 mol (10.6 g) of 2,6-dinitro-4-methylanisole is dissolved in 50 ml of absolute alcohol. 0.1 mol (9.1 g) of 1-aminopropane-2,3-diol is added gradually to this solution, whilst stirring. The solution is heated under reflux for 3 hours 30 minutes. The alcohol is driven off in vacuo and 40 ml of iced water are added to the residual red oil. The expected product crystallises. It is filtered off and washed with water. After recrystallisation from an aqueous-alcoholic mixture and drying in vacuo, it melts at 118° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 3 hours 30 minutes
  3. additionare added to the residual red oil
  4. customThe expected product crystallises
  5. filtrationIt is filtered off
  6. washwashed with water
  7. customAfter recrystallisation from an aqueous-alcoholic mixture
  8. customdrying in vacuo, it melts at 118° C.

Sources & evidence

ORD record
ord-434fa734567a434581b53d7c61d70a42
Source dataset
uspto-grants-1993_02
Patent number
US05186717

Reaction notes

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