2-Ethyl-6-methylaniline → HCID 12546900, compound

HRID 1732240Notes

Reaction equation

HRID 1732240 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:4]=1[NH2:5])[CH3:2].[Br:11][CH2:12][CH2:13][C:14](Cl)=[O:15].O.O.O.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[Br:11][CH2:12][CH2:13][C:14]([NH:5][C:4]1[C:6]([CH3:10])=[CH:7][CH:8]=[CH:9][C:3]=1[CH2:1][CH3:2])=[O:15]

Participants

6

Reactant 3

HCID 324852-Ethyl-6-methylanilineHCID 84944Propanoyl chloride, 3-bromo-HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12546900HCID 12546900, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a glass-stoppered bottle, a solution of 2-ethyl-6-methylaniline (15.0 g, 0.111 mole) in glacial acetic acid (95 ml) was cooled to 13° C. and 3-bromo-propionyl chloride (21.1 g, 0.122 mole) was added. The mixture was mixed and was combined immediately with a cooled (3° C.) solution of sodium acetate trihydrate (36.9 g) in water (150 ml). The mixture was shaken vigorously for 30 min. The white product that formed was filtered off, washed carefully with water, and dried. This product, i.e., 3-bromo-2'-ethyl-6'-methylpropionanilide (27.4 g, 91%), melted at 149°-150° C. and was sufficiently pure for the next step.

Workup

  1. additionThe mixture was mixed
  2. customThe white product that formed
  3. filtrationwas filtered off
  4. washwashed carefully with water
  5. customdried

Sources & evidence

ORD record
ord-4feefa59677d4fa6bf33ae8dce1e174b
Source dataset
uspto-grants-1980_12
Patent number
US04237068

Reaction notes

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