Benzoyl chloride → HCID 18987267, compound

HRID 2396515Notes

Reaction equation

HRID 2396515 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[OH-].[K+]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.O.C(O)C>[C:38]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:9]=2)=[CH:4][CH:3]=1)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 10431342HCID 10431342, compound

Product 1

HCID 18987267HCID 18987267, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 6-{[4-(4-aminophenyl)-6-phenyl-2-pyridyl]oxy}hexanoate (4 g), triethylamine (1.7 cc) and a spatula-tip-full of 4dimethylaminopyridine (DMAP) in chloroform (40 cc), is slowly added, at room temperature, benzoyl chloride (1.38 cc) in solution in chloroform (20 cc). The temperature rises up to 33° C. The reaction mixture is then stirred at room temperature for 21 hours and then hydrolysed with distilled water (50 cc). The organic phase is decanted. The aqueous phase is extracted with dichloromethane (2×50 cc). The combined organic phases are washed with distilled water until neutrality, dried over sodium sulphate and concentrated to dryness at 40° C. under reduced pressure. The product is used directly in the next reaction after purification by recrystallization in an n-hexane-ethyl acetate (1-1) mixture (100 cc). The procedure in Example 3 is then followed but using the ethyl 6-{[4-(4-benzamidophenyl)-6-phenyl-2-pyridyl]oxy}hexanoate previously obtained, potassium hydroxide pellets (0.7 g) dissolved in distilled water (15 cc) and ethanol (150 cc). The reaction mixture is refluxed for 2 hours. The product is purified by recrystallization in ethyl acetate (50 cc), whitish crystals (m.p.=167°-169° C.)

Workup

  1. customrises up to 33° C
  2. customThe organic phase is decanted
  3. extractionThe aqueous phase is extracted with dichloromethane (2×50 cc)
  4. washThe combined organic phases are washed with distilled water until neutrality
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure
  7. customThe product is used directly in the next reaction
  8. customafter purification
  9. customby recrystallization in an n-hexane-ethyl acetate (1-1) mixture (100 cc)
  10. custompreviously obtained
  11. temperatureThe reaction mixture is refluxed for 2 hours
  12. customThe product is purified by recrystallization in ethyl acetate (50 cc)

Sources & evidence

ORD record
ord-956a27bb1f3b4bb29a69371e0a766c13
Source dataset
uspto-grants-1996_02
Patent number
US05492915

Reaction notes

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