Triethylamine → HCID 178483602, compound

HRID 2276007Notes

Reaction equation

HRID 2276007 reaction equation
[CH3:1][NH:2][C:3]([CH3:9])=[CH:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[Cl:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:19]=1[C:20](=[O:21])[C:4](=[C:3]([NH:2][CH3:1])[CH3:9])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734182Methyl 3-(methylamino)but-2-enoate2×HCID 27365462-Chloro-4-fluorobenzoyl chloride

Product 1

HCID 178483602HCID 178483602, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a mixture of methyl 3-(methylamino)-2-butenoate (i.e. the product of Step A) (10.25 g, 79.43 mmol) and triethylamine (13.26 mL, 9.63 g, 95.31 mmol) in toluene (125 mL) at 0° C. was added dropwise 2-chloro-4-fluorobenzoyl chloride (15.25 g, 79.48 mol) in toluene (25 mL) over 30 minutes while maintaining the temperature of the reaction mixture between about 0 to 5° C. The reaction mixture was allowed to warm to room temperature and stirred over night. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting dark yellow oil was triturated with hexanes and filtered to provide the title compound as a white solid (15.91 g).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting dark yellow oil was triturated with hexanes
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9547ead4b53c4edc8253179d4ae48f9b
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Reaction notes

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