Water → HCID 13491698, compound

HRID 463797Notes

Reaction equation

HRID 463797 reaction equation
[CH3:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10](N(CC)CC)[CH3:11].C(Br)C.O>C1C=CC=CC=1>[CH2:10]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:2]=1[CH3:1])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 68943-Chloro-2-methylanilineHCID 8471Triethylamine

Product 1

HCID 13491698HCID 13491698, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In 100 ml of benzene is dissolved 14 g of 2-methyl-3-chloroaniline obtained in Reference Example 1 and, after adding 12 g of triethylamine, 13 g of ethyl bromide is added to the solution to conduct the reaction under reflux of benzene for 3 hours. After the completion of the reaction, the mixture is cooled to room temperature and shaken with 200 ml of water. The benzene layer is separated, dried over anhydrous magnesium sulfate, and concentrated. Distillation of the residue results in 12 g of N-ethyl-2-methyl-chloroaniline as the fraction of 125°-126° C./10 mmHg.

Workup

  1. customobtained in Reference Example 1
  2. additionis added to the solution
  3. customthe reaction
  4. customAfter the completion of the reaction
  5. customThe benzene layer is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. distillationDistillation of the residue
  9. customresults in 12 g of N-ethyl-2-methyl-chloroaniline as the fraction of 125°-126° C./10 mmHg

Sources & evidence

ORD record
ord-a609d273a363402e9668b69a7fb72c5d
Source dataset
uspto-grants-1985_10
Patent number
US04544747

Reaction notes

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