Hydrochloric Acid → HCID 18469985, compound

HRID 2228451Notes

Reaction equation

HRID 2228451 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S.O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:13](=[O:14])[CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 797124-(4-Nitrophenyl)butyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18469985HCID 18469985, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 4-(4-nitrophenyl)butyryl chloride (5.4 g, 23.7 mmol) and 4-fluorobenzene (2.6 mL, 26.2 mmol) dissolved in carbon disulfide (25 mL) was treated in portions with aluminum chloride (4.1 g, 30.75 mmol) under a nitrogen atmosphere. After the addition was complete, the reaction mixture was heated to 60-70° C. for about 12 hours. The resulting mixture was cooled in an ice bath, treated with concentrated hydrochloride acid (12 mL), and stirred for 30 minutes. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with 1 N aqueous sodium hydroxide, water, and brine, dried and evaporated in vacuo. Purification by silica gel chromatography, eluting with 5% ethyl acetate/hexane gave the title compound as a white solid (3.81 g, 56%). The product was used in the next step.

Workup

  1. additionAfter the addition
  2. temperatureThe resulting mixture was cooled in an ice bath
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with 1 N aqueous sodium hydroxide, water, and brine
  6. customdried
  7. customevaporated in vacuo
  8. customPurification by silica gel chromatography
  9. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-547e6f69089047ea89424cfc1a19edb1
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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