Triethylamine → HCID 54054125, compound

HRID 651605Notes

Reaction equation

HRID 651605 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]([OH:16])=O)[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CC(C)=O.O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]([N:30]=[N+:31]=[N-:32])=[O:16])[CH:8]=[CH:9][C:10]=1[CH3:11])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 545379543-[3-(Acetylamino)-4-methylphenyl]-2-propenoic acid

Product 1

HCID 54054125HCID 54054125, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a slurry of 3-(3-acetamido-4-methylphenyl)propenoic acid (20.11 g, 91.7 mmol) in acetone (450 mL) at 0° C. is added triethylamine (12.8 mL, 91.8 mmol) followed by dropwise addition of ethyl chloroformate (11.8 mL, 123 mmol) over a 10 minutes period. The resulting yellow slurry is stirred using a mechanical stirrer for 1.5 hours, then a solution of sodium azide (8.94 g, 138 mmol) in water (25 mL) is added slowly so as to maintain the temperature below 5° C. The thick mixture is stirred at 0° C. for 1 hours, then the ice bath is removed and the reaction mixture allowed to warm to room temperature. The suspension is poured over water (800 mL) then filtered. The remaining solid is washed generously with water and dried under vacuum over P2O5 overnight to give the product as a pale yellow solid (21.40 g, 87.6 mmol).

Workup

  1. customfor 1.5 hours
  2. temperatureto maintain the temperature below 5° C
  3. stirringThe thick mixture is stirred at 0° C. for 1 hours
  4. customthe ice bath is removed
  5. additionThe suspension is poured over water (800 mL)
  6. filtrationthen filtered
  7. washThe remaining solid is washed generously with water
  8. dry with materialdried under vacuum over P2O5 overnight

Sources & evidence

ORD record
ord-2e2fd06c5f23471abb43fbb716277512
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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