Water → HCID 19827790, compound

HRID 223407Notes

Reaction equation

HRID 223407 reaction equation
Cl.Cl.[CH3:3][NH:4][C:5]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:6]=1[NH2:7].[OH-].[Na+].O.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19]>C1(C)C(C)=CC=CC=1>[CH3:3][N:4]1[C:5]2[C:6](=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[NH:7][C:18](=[O:19])[C:17]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 12198275HCID 12198275, compound

Product 1

HCID 19827790HCID 19827790, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Methylamino-5-methoxyaniline dihydrochloride (0.256 mol) is neutralized with sodium hydroxide (22 g., 0.5 mol) in 80 ml. of water. The free amine is extracted into 300 ml. of xylene, the solution dried over magnesium sulfate, and filtered. This solution is then added over 50 min. to a solution of oxalyl chloride (39 g., 0.307 mol) in 300 ml. of xylene held at 75°-90° C. After addition is complete, the resulting solution is heated to a bath temperature of 155° and then allowed to cool to room temperature. The flask is cooled to 0° and the gray precipitate collected by vacuum filtration. The solid product is then dried under high vacuum at 160° for two hours.

Workup

  1. extractionThe free amine is extracted into 300 ml
  2. dry with materialof xylene, the solution dried over magnesium sulfate
  3. filtrationfiltered
  4. customheld at 75°-90° C
  5. additionAfter addition
  6. temperaturethe resulting solution is heated to a bath temperature of 155°
  7. temperatureThe flask is cooled to 0°
  8. filtrationthe gray precipitate collected by vacuum filtration
  9. customThe solid product is then dried under high vacuum at 160° for two hours

Sources & evidence

ORD record
ord-fa9d3e7f26d048909aec02abb02e72b3
Source dataset
uspto-grants-1982_10
Patent number
US04354027

Reaction notes

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