Quinoline → HCID 14255701, compound

HRID 580250Notes

Reaction equation

HRID 580250 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15][CH2:16][CH:17]=C)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C2C(=CC=CC=2)C=C[CH:20]=1.C(OCC)(=O)C>CCCCCC>[C:1]([NH:5][S:6]([C:9]1[C:10]2[S:15][CH:16]([CH3:17])[CH2:20][C:11]=2[CH:12]=[CH:13][CH:14]=1)(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 8857Ethyl AcetateHCID 14255699N-tert-Butyl-2-[(prop-2-en-1-yl)sulfanyl]benzene-1-sulfonamide

Product 1

HCID 14255701HCID 14255701, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of 89.9 g of N-t-butyl-2-(2-propenylthio)benzenesulfonamide and quinoline (90 ml) were heated at 220° C. for 2 hours under an inert atmosphere. The mixture was cooled, was poured into ice-water (500 ml) and was extracted with several portions of a 1:1 mixture of chlorobutane and tetrahydrofuran. The combined extracts were washed with 6N hydrochloric acid and brine. The organic mixture was dried over magnesium sulfate and was concentrated. The residue was distilled in a kugelrohr apparatus at 170°-200° C. (1 torr), giving after trituration with chlorobutane and hexane a yellow solid. Chromatography of the mixture on silica gel eluting with 20% ethyl acetate in hexane afforded after recrystallization from hexanechlorobutane the title compound as a white solid, m.p. 97°-98° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionwas extracted with several portions of a 1:1 mixture of chlorobutane and tetrahydrofuran
  3. washThe combined extracts were washed with 6N hydrochloric acid and brine
  4. dry with materialThe organic mixture was dried over magnesium sulfate
  5. concentrationwas concentrated
  6. distillationThe residue was distilled in a kugelrohr apparatus at 170°-200° C. (1 torr)
  7. customgiving after trituration with chlorobutane and hexane a yellow solid
  8. customafter recrystallization from hexanechlorobutane the title compound as a white solid, m.p. 97°-98° C.

Sources & evidence

ORD record
ord-439e271cac5042aea1a24b76118ef645
Source dataset
uspto-grants-1988_06
Patent number
US04752322

Reaction notes

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