Hydrochloric Acid → HCID 71062657, compound

HRID 1479127Notes

Reaction equation

HRID 1479127 reaction equation
CC(C)([O-])C.[Na+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[I:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1.Cl>O1CCCC1.C1(C)C=CC=CC=1.CN1CCCC1=O.O1CCCC1.CN1CCCC1=O>[I:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:22]#[N:23])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 81001,5-DibromopentaneHCID 1428664-IodophenylacetonitrileHCID 23676156Sodium t-butoxide

Product 1

HCID 71062657HCID 71062657, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 22156051tetrahydrofuran N-methylpyrrolidinoneSolvent

Conditions

Temperature
0 °C

Procedure

N-Methylpyrrolidinone (NMP) (197 mL, Sigma-Aldrich) was added to a suspension of sodium tert-butoxide (124.0 g, Alfa-Aesar) in tetrahydrofuran (THF) (197 mL, Univar) under argon. The mixture was cooled to 0° C. and a solution of 1,5-dibromopentane (87.9 mL, Sigma-Aldrich) and 4-iodophenylacetonitrile (78.4 g) in a 50:50 mixture of NMP/THF (173 mL) was added dropwise keeping the internal temperature below 10° C. The mixture was warmed to room temperature and stirred overnight. 2M hydrochloric acid (930 mL) and toluene (930 mL) were added then the aqueous layer was separated and extracted with toluene (2×465 mL). The combined organics were washed with saturated sodium bicarbonate (930 mL), brine (930 mL), 2M sodium thiosulfate (930 mL), dried (magnesium sulphate) and concentrated in vacuo to a yellow/orange solid. Dichloromethane was added and the solid was filtered and washed with dichloromethane to give the product as a white solid. Yield: 22.55 g. 1H NMR (400 MHz, CDCl3): δ 7.70-7.72 (2H, m, ArH), 7.22-7.25 (2H, m, ArH), 2.10-2.13 (2H, m, —CH2—), 1.67-1.89 (7H, m, —CH—), 1.22-1.32 (1H, m, —CH—).

Workup

  1. additionwas added dropwise
  2. customthe internal temperature below 10° C
  3. temperatureThe mixture was warmed to room temperature
  4. customthe aqueous layer was separated
  5. extractionextracted with toluene (2×465 mL)
  6. washThe combined organics were washed with saturated sodium bicarbonate (930 mL), brine (930 mL), 2M sodium thiosulfate (930 mL)
  7. dry with materialdried (magnesium sulphate)
  8. concentrationconcentrated in vacuo to a yellow/orange solid
  9. additionDichloromethane was added
  10. filtrationthe solid was filtered
  11. washwashed with dichloromethane

Sources & evidence

ORD record
ord-69edd6bf4938498db4e03da959f9dfea
Source dataset
uspto-grants-2016_08
Patent number
US09406886B2

Reaction notes

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