Triethylamine → HCID 54140071, compound

HRID 2398097Notes

Reaction equation

HRID 2398097 reaction equation
[N+:1]([C:4]1[O:8][C:7]([CH:9]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][CH:12](C)[C:13](Cl)=O.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:11][C:12]([CH3:13])=[CH:9][C:7]1[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127745-NitrofurfuralHCID 1110192-Chloropropionyl chloride

Product 1

HCID 54140071HCID 54140071, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 9 g of 5-nitro-2-furaldehyde and 11.0 g of 2-chloropropionyl chloride in 100 ml of benzene was added dropwise at 25°-30° over a 20-minute period a solution of 10 g of triethylamine in 30 ml of benzene. After an additional 40 minutes, the mixture was stirred at reflux for 1.5 hours. The cooled mixture was washed with water, dried and concentrated under reduced pressure to leave a residue which was distilled to give a liquid product, b.p.: 92°-100° at 0.15 torr. This product was triturated with n-hexane to give 3 as a mixture of stereisomers, a tan solid, m.p.: 55°-65°.

Workup

  1. temperatureat reflux for 1.5 hours
  2. washThe cooled mixture was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customto leave a residue which
  6. distillationwas distilled
  7. customto give a liquid product, b.p.: 92°-100° at 0.15 torr
  8. customThis product was triturated with n-hexane
  9. customto give 3
  10. additionas a mixture of stereisomers

Sources & evidence

ORD record
ord-3090cbd05e9a434a99bbd1b68f204755
Source dataset
uspto-grants-1977_05
Patent number
US04024161

Reaction notes

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