Potassium Carbonate → HCID 22006769, compound

HRID 323663Notes

Reaction equation

HRID 323663 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:27])[CH:6]=[C:7]([CH3:26])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:34][C:35]([Cl:39])=[CH:36][CH2:37]Cl>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[C:5]([O:27][CH2:37][CH:36]=[C:35]([Cl:39])[Cl:34])[CH:6]=[C:7]([CH3:26])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:25])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 22006724HCID 22006724, compound

Product 1

HCID 22006769HCID 22006769, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.66 g of 3-ethyl-5-methyl-4-(3-(4-(trifluoromethyl)benzamido)propyloxy)phenol, 0.29 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a mixed solution of 0.28 g of 1,1,3-trichloropropene and 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 6 hours, the reaction mixture was poured into ice water and extracted twice with 50 ml of diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give crude crystals. The crude crystals were ground and washed with n-hexane, which afforded 0.48 g of 3-ethyl-5-methyl-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-(trifluoromethyl)benzamido)propyloxy)benzene (58% yield), m.p., 92.2° C.

Workup

  1. stirringAfter stirring at room temperature for 6 hours
  2. extractionextracted twice with 50 ml of diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give crude crystals
  7. washwashed with n-hexane, which

Sources & evidence

ORD record
ord-7bda2ae4f47e40388d851c321e3749d1
Source dataset
uspto-grants-2001_04
Patent number
US06214835B1

Reaction notes

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