Ethanol → HCID 178470062, compound

HRID 1602304Notes

Reaction equation

HRID 1602304 reaction equation
C([CH:3]([C:7]([Cl:9])=O)C(Cl)=O)C.[Cl:10][C:11]1[C:12]([O:22][CH3:23])=[CH:13][CH:14]=[C:15]([CH:21]=1)[NH:16][C:17](=[O:20])[CH2:18]Cl.C(N(CC)CC)C.[CH2:31]([O-:33])[CH3:32].[Na+].[CH2:35]([OH:37])C>C(#N)C.O>[Cl:10][C:11]1[CH:21]=[C:15]2[C:14]([C:3]([CH2:7][Cl:9])=[C:18]([C:35]([O:33][CH2:31][CH3:32])=[O:37])[C:17]([OH:20])=[N:16]2)=[CH:13][C:12]=1[O:22][CH3:23]

Participants

8

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 24048042-chloro-N-(3-chloro-4-methoxyphenyl)acetamideHCID 2723922Sodium ethoxideHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 178470062HCID 178470062, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Ethylmalonyl chloride (17 ml, 131 mmol) is added drop-wise to a solution of 5-chloro-2-chloroacetyl-4-methoxyaniline (17 g, 73 mmol) and triethylamine (18.5 ml, 131 mmol) in anhydrous acetonitrile (310 ml), under argon and at 0° C. Agitate for 2 h at ambient temperature, then add drop-wise at 0° C. a solution of sodium ethanolate in ethanol (obtained by 1.88 g, 80 mmol, of sodium in 90 ml of ethanol). Agitated for 12 hours at ambient temperature. Add 300 ml of water, agitate for another 20 minutes. Filter the precipitate; wash with water, ethanol, and ethyl ether. After drying in vacuum, 16.7 g of a yellowish solid is obtained.

Workup

  1. customat 0° C
  2. stirringAgitated for 12 hours at ambient temperature
  3. stirringagitate for another 20 minutes
  4. filtrationFilter the precipitate
  5. washwash with water, ethanol, and ethyl ether
  6. customAfter drying in vacuum

Sources & evidence

ORD record
ord-f68a857a0e3448358c1c8176eff7a549
Source dataset
uspto-grants-1999_11
Patent number
US05981542

Reaction notes

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