Triethylamine → N-(2-Methylbenzo[d]oxazol-5-yl)acrylamide

HRID 5506Notes

Reaction equation

HRID 5506 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>O1CCCC1>[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1)(=[O:22])[CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 19796105N-(2-Methylbenzo[d]oxazol-5-yl)acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

About 150 parts of (2) are dissolved in about 1200 ml of warm tetrahydrofuran in a 3 liter three-necked flask equipped with a mechanical stirrer and dropping funnel. About 113 parts of triethylamine are added to the flask and then cooled to 0° C. using an ice bath. About 100 parts of acryloyl chloride are combined with about 300 ml of tetrahydrofuran in a dropping funnel and added dropwise to the flask while stirring under dry nitrogen. The mixture in the flask is allowed to return to room temperature while being stirred overnight and then filtered. The filter is stirred in about 1 liter of warm tetrahydrofuran for about thirty minutes and filtered again. Both filtrates are combined and about 10 ml of nitrobenzene are added to inhibit polymerization. Solvent is removed using a rotary evaporator and ethyl ether is added to solidify the product. The dark brown solid obtained after filtering is washed with methylene chloride, then ethyl ether to provide 5-acrylamido-2-methyl benzoxazole (3) as a tan solid after drying under vacuum.

Workup

  1. customequipped with a mechanical stirrer
  2. additionadded dropwise to the flask
  3. customto return to room temperature
  4. stirringwhile being stirred overnight
  5. filtrationfiltered
  6. stirringThe filter is stirred in about 1 liter of warm tetrahydrofuran for about thirty minutes
  7. filtrationfiltered again
  8. additionabout 10 ml of nitrobenzene are added
  9. custompolymerization
  10. customSolvent is removed
  11. customa rotary evaporator and ethyl ether
  12. additionis added
  13. customThe dark brown solid obtained
  14. filtrationafter filtering
  15. washis washed with methylene chloride

Sources & evidence

ORD record
ord-cbdf37bd45334f7f8694cc9857bcf8c9
Source dataset
uspto-grants-1993_09
Patent number
US05244994

Reaction notes

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