Benzaldehyde → HCID 58696280, compound

HRID 1178321Notes

Reaction equation

HRID 1178321 reaction equation
C(N(CC)CC)C.[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[NH2:17][CH:18]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(#N)C>[CH2:22]([O:21][C:19](=[O:20])[CH:18]([N:17]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[CH3:23]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 6949597672954-97-3

Product 1

HCID 58696280HCID 58696280, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (170 mL) and benzaldehyde (130 mL) were added to a suspension of ethyl amino-(3,4-dichlorophenyl)-acetate hydrochloride (350 g) in acetonitrile (1.5 L), followed by stirring at room temperature overnight. The insoluble matter was removed through Celite, followed by washing with ethyl acetate. The filtrate was subjected to partitioning with water and then extraction with ethyl acetate. The thus-obtained organic layer was washed with saturated brine, and then dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure, to thereby give the title compound (425 g). The title compound was used in the next step without further purification.

Workup

  1. customThe insoluble matter was removed through Celite
  2. washby washing with ethyl acetate
  3. customto partitioning with water
  4. extractionextraction with ethyl acetate
  5. washThe thus-obtained organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydrate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-05cd4704ccac4b3185bf5dea055323e5
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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