Ethanol → HCID 21892028, compound

HRID 1884070Notes

Reaction equation

HRID 1884070 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](=[O:20])[NH: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 21892028HCID 21892028, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ethylmalonyl chloride (17 ml, 131 mmol) is added dropwise under argon and at 0° C. 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). Agitation is carried out for 2 hours at ambient temperature, then a solution of sodium ethanolate in ethanol (obtained by 1.88 g, 80 mmol, of sodium in 90 ml of ethanol) is added dropwise at 0C. Agitation is carried out for 12 hours at ambient temperature. 300 ml of water is added, and agitation is again carried out for 20 minutes. The precipitate is filtered out; washed with water, with ethanol, and with ethyl ether. After drying under vacuum 16.7 g of a yellowish solid is obtained.

Workup

  1. waitAgitation is carried out for 12 hours at ambient temperature
  2. waitagitation is again carried out for 20 minutes
  3. filtrationThe precipitate is filtered out
  4. washwashed with water, with ethanol
  5. dry with materialAfter drying under vacuum 16.7 g of a yellowish solid
  6. customis obtained

Sources & evidence

ORD record
ord-7d2f64ed4d084a5ab0b25eb31bf2538c
Source dataset
uspto-grants-2004_07
Patent number
US06762301B2

Reaction notes

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