Water → 4-Chloro-3-(3-methyl-2-butenyloxy)phenyl-2-methyl-3-furancarboxamide

HRID 50016Notes

Reaction equation

HRID 50016 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7](Cl)=[O:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](N)=[CH:13][C:12]=1[O:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22].C([N:26](CC)CC)C.O>C(Cl)Cl>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:5]2[C:6]([C:7]([NH2:26])=[O:8])=[C:2]([CH3:1])[O:3][CH:4]=2)=[CH:13][C:12]=1[O:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27598502-Methylfuran-3-carbonyl chlorideHCID 129856914-Chloro-3-(3-methyl-2-butenyloxy)benzenamine

Product 1

HCID 867517074-Chloro-3-(3-methyl-2-butenyloxy)phenyl-2-methyl-3-furancarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A first solution of 2-methyl-3-furancarboxylic chloride (13.57 g) in methylene chloride (94 mL) was stirred in an ice/salt bath. A second solution of 4-chloro-3-(3-methyl-2-butenyloxy)benzenamine (19.8 g), triethylamine (14 mL) in methylene chloride (94 mL) was added to the first solution at such a rate that the temperature was maintained at −5° C. to 0° C. When the addition was complete, the resultant reaction mixture was stirred to ambient temperature and left stirring for 15 hours. Water was added to the reaction mixture and then the organic layer separated and washed successively with water, dilute hydrochloric acid, water, aqueous sodium bicarbonate, and water. After drying (MgSO4), the solvent was removed from the washed organic layer and the residue was recrystallised from isopropyl alcohol to give N-[4-chloro-3-(3-methyl-2-butenyloxy)phenyl-2-methyl-3-furancarboxamide, a white solid, 17 g. A second crop of beige crystals, 7.6 g, was also obtained.

Workup

  1. temperaturewas maintained at −5° C. to 0° C
  2. additionWhen the addition
  3. customthe resultant reaction mixture
  4. waitleft
  5. stirringstirring for 15 hours
  6. customthe organic layer separated
  7. washwashed successively with water, dilute hydrochloric acid, water, aqueous sodium bicarbonate, and water
  8. dry with materialAfter drying (MgSO4)
  9. customthe solvent was removed from the washed organic layer
  10. customthe residue was recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-1598fac10b0249b0813aaa23d3c52548
Source dataset
uspto-grants-2004_03
Patent number
US06710077B1

Reaction notes

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