Water → HCID 10957003, compound

HRID 2073999Notes

Reaction equation

HRID 2073999 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([O:8][C:9]1[CH:18]=[C:17]([NH2:19])[C:16]([Cl:20])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH2:7].O>N1C=CC=CC=1>[CH2:5]([O:8][C:9]1[CH:18]=[C:17]([NH:19][C:1](=[O:3])[CH3:2])[C:16]([Cl:20])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 14883224HCID 14883224, compound

Product 1

HCID 10957003HCID 10957003, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (6.5 g) is added dropwise to a stirring solution of the amine of step 4 above (5 g) in pyridine (80 ml) cooled in an ice bath. The reaction mixture is allowed to warm to RT with stirring for 45 minutes. Water is added, the mixture again cooled in ice, and partitioned between H2O and CH2Cl2. The organic layer is separated and washed successively with H2O, 10% HCl, aqueous saturated NaHCO3, dried, filtered and evaporated affording a solid residue which is recrystallized from Hexane-Ethyl acetate, M.P. 110°-112° C. NMR (90 MHz, DMSO-d6) shows the correct compound.

Workup

  1. temperaturecooled in an ice bath
  2. temperaturethe mixture again cooled in ice
  3. custompartitioned between H2O and CH2Cl2
  4. customThe organic layer is separated
  5. washwashed successively with H2O, 10% HCl, aqueous saturated NaHCO3
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customaffording a solid residue which
  10. customis recrystallized from Hexane-Ethyl acetate, M.P. 110°-112° C

Sources & evidence

ORD record
ord-6c2d656fcbc34836a34ed6638e5a598b
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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