4-Chlorobenzoyl chloride → HCID 53697856, compound

HRID 1975389Notes

Reaction equation

HRID 1975389 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>C(N(CC)CC)C>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:4][CH:3]=2)=[O:29])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 53838801HCID 53838801, compound

Product 1

HCID 53697856HCID 53697856, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

At 5°-10° C., 5 ml of triethylamine are added dropwise to a mixture of 3 g of methyl 6-(4-aminophenyl)-6-(3-pyridyl)-hex-5-enoate and 2.1 g of 4-chlorobenzoic acid chloride. After 30 minutes the reaction mixture is washed with water and evaporated down. The residue is mixed with 30 ml of ethanol and 5 ml of 10N sodium hydroxide solution and heated to 50° C. for 30 minutes. The reaction mixture is evaporated down and the residue is taken up in water. The agueous phase is washed with ethyl acetate, neutralised by the addition of citric acid and then extracted with ethyl acetate. The organic phase is washed with water, dried and evaporated down and the residue is recrystallised from ethyl acetate/diisopropylether.

Workup

  1. washAfter 30 minutes the reaction mixture is washed with water
  2. customevaporated down
  3. additionThe residue is mixed with 30 ml of ethanol and 5 ml of 10N sodium hydroxide solution
  4. customThe reaction mixture is evaporated down
  5. washThe agueous phase is washed with ethyl acetate
  6. additionneutralised by the addition of citric acid
  7. extractionextracted with ethyl acetate
  8. washThe organic phase is washed with water
  9. customdried
  10. customevaporated down
  11. customthe residue is recrystallised from ethyl acetate/diisopropylether

Sources & evidence

ORD record
ord-cf57c0ec7b8a4848b99b723e5f5501f0
Source dataset
uspto-grants-1994_02
Patent number
US05286736

Reaction notes

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