1-Propanol → HCID 20554734, compound

HRID 1105743Notes

Reaction equation

HRID 1105743 reaction equation
[CH3:1][N:2]([C:14]1[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=1)[C:3]1[N:4]=[N:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:7]=2[N:8]=1.[CH2:28](O)CC.S(=O)(=O)(O)O>O>[CH3:1][N:2]([C:14]1[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH2:24][CH3:28])=[O:21])=[CH:16][CH:15]=1)[C:3]1[N:4]=[N:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 1118Sulfuric AcidHCID 15587058HCID 15587058, compound

Product 1

HCID 20554734HCID 20554734, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 2-{4-[N-methyl-N-(7-chloro-1,2,4-benzotriazin-3-yl)amino]phenoxy}propionate (80 g, compound No. 21, Example 7), n-propanol (800 ml) and concentrated sulfuric acid (3 ml) was heated under reflux for a period of 6 hours. A small volume of water was added and the mixture was concentrated. Dichloromethane was added and the mixture was washed first with dilute aqueous potassium carbonate solution and then with water. The organic phase was dried (over anhydrous magnesium sulfate) and the solvent was removed by distillation under reduced pressure to give the title compound (80 g) as a red oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 6 hours
  3. concentrationthe mixture was concentrated
  4. additionDichloromethane was added
  5. washthe mixture was washed first with dilute aqueous potassium carbonate solution
  6. dry with materialThe organic phase was dried (over anhydrous magnesium sulfate)
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-65587d85f1564d99bfbd77bb7e14b66b
Source dataset
uspto-grants-1982_01
Patent number
US04310347

Reaction notes

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