Ethanol → HCID 22184598, compound

HRID 1795052Notes

Reaction equation

HRID 1795052 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[Na].CCO.[Cl:20][C:21]1[CH:26]=[C:25]([CH2:27]Cl)[CH:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[C:22]=1[NH2:33]>O1CCOCC1.O>[C:1]([NH:4][C:5]([CH2:27][C:25]1[CH:24]=[C:23]([C:29]([F:31])([F:32])[F:30])[C:22]([NH2:33])=[C:21]([Cl:20])[CH:26]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 22184588HCID 22184588, compound2×

Product 1

HCID 22184598HCID 22184598, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

24.11 g (0.11 mol) diethyl 2-acetylamino-malonate was added to a freshly prepared solution of 2.55 g (0.11 mol) sodium in 200 mL abs. EtOH under a nitrogen atmosphere and the mixture was stirred for 15 minutes at RT. A solution of 27.00 g (0.11 mol) 2-chloro-4-chlormethyl-6-trifluoromethyl-phenylamine (Intermediate product 55) in 100 mL 1,4-dioxane was rapidly added dropwise and the mixture was stirred for 4 hours at RT. 500 mL water were added and the mixture was stirred for a further 16 hours. The precipitate formed was filtered off, washed with water and dried i. vac.

Workup

  1. stirringthe mixture was stirred for a further 16 hours
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customdried i

Sources & evidence

ORD record
ord-0d9f3935ab5d4ea7aede39728000bea0
Source dataset
uspto-grants-2006_04
Patent number
US07026312B2

Reaction notes

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