Potassium Carbonate → HCID 22145734, compound

HRID 356896Notes

Reaction equation

HRID 356896 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[C:21](Cl)=[O:22])[CH2:16][CH:15]=[CH:14][CH2:13]1.C1(OC2C=C(C=CC=2OC)C(O)=O)CC=CC1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:9][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([Cl:8])[C:2]=1[NH:1][C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:18]([O:17][CH:12]2[CH2:13][CH:14]=[CH:15][CH2:16]2)[CH:19]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 898884-Amino-3,5-dichloropyridineHCID 22145730HCID 22145730, compoundHCID 22145794HCID 22145794, compound

Product 1

HCID 22145734HCID 22145734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-amino-3,5-dichloropyridine (0.93 g) in dry tetrahydrofuran (56 mL) under nitrogen at 5°-10° C. is treated portionwise with sodium hydride (60% dispersion in oil, 0.57 g). After 1 hour it is treated dropwise with a solution of 3-cyclopent-3-enyloxy-4-methoxybenzoyl chloride in dry tetrahydrofuran (30 mL) prepared as described in Reference Example 33 from 1.33 g 3-cyclopent-3-enyloxy-4-methoxybenzoic acid). The resulting mixture is allowed to warm to room temperature, stirred for a further 3 hours and then poured into 5% aqueous potassium carbonate (430 mL). The resulting emulsion is extracted with ethyl acetate (3×150 mL), the combined organic extracts washed with water (2×20 mL), followed by ice-cold 1 M aqueous hydrochloric acid (2×20 mL) and dried over sodium sulfate. The solvent is removed under reduced pressure and the resulting residue subject to flash chromatography on silica gel, eluting with mixtures of t-butyl methyl ether and cyclohexane (2:3 to 7:3 v/v), to give a cream solid, which is recrystallized from acetonitrile to give N-(3,5-dichloropyrid-4-yl)-3-cyclopent-3-enyloxy-4-methoxybenzamide (0.54 g), as a white solid, m.p. 193°-195° C. [Elemental analysis: C,56.7; H,4.2; N,7.3%; calculated: C,57.0; H,4.3; N,7.4%].

Workup

  1. customprepared
  2. extractionThe resulting emulsion is extracted with ethyl acetate (3×150 mL)
  3. washthe combined organic extracts washed with water (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. washeluting with mixtures of t-butyl methyl ether and cyclohexane (2:3 to 7:3 v/v)
  7. customto give a cream solid, which
  8. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1c611c352689410c8a04a3fc11b124a1
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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