Dichloroacetyl chloride → HCID 4158166, compound

HRID 2398095Notes

Reaction equation

HRID 2398095 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]([Cl:16])C(Cl)=O.C(N(CC)CC)C>C1C=CC=CC=1>[Cl:11][C:12]([Cl:16])=[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 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 127745-Nitrofurfural

Product 1

HCID 4158166HCID 4158166, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred mixture of 14.1 g of 5-nitro-2-furaldehyde and 22.1 g of dichloroacetyl chloride in 300 ml of benzene was added dropwise at 25°-30° over a 30-minute period a solution of 15.2 g of triethylamine in 50 ml of benzene. The mixture then was stirred at 25°-30° for an additional 30 minutes and then for 90 minutes at reflux. After cooling, the mixture was filtered and the filtrate was washed and dried, concentrated under reduced pressure and Claisen distilled to give a liquid product, b.p.: 88°-98° at 0.3 torr. (mainly 90°-95°). This material was crystallized from acetone/petroleum ether to give 1 as a light yellow solid, m.p.: 74°-75°.

Workup

  1. temperaturefor 90 minutes at reflux
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washthe filtrate was washed
  5. customdried
  6. concentrationconcentrated under reduced pressure and Claisen
  7. distillationdistilled
  8. customto give a liquid product, b.p.: 88°-98° at 0.3 torr
  9. custommainly 90°-95°
  10. customThis material was crystallized from acetone/petroleum ether

Sources & evidence

ORD record
ord-daaaeac386c348b5bb5b6df8d0063b5f
Source dataset
uspto-grants-1977_05
Patent number
US04024161

Reaction notes

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