Triethylamine → HCID 59378874, compound

HRID 2201624Notes

Reaction equation

HRID 2201624 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[F:13][C:14]1[CH:15]=[C:16]([SH:20])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C.CCCCCCC>CN1C(=O)CCC1.O>[F:13][C:14]1[CH:15]=[C:16]([S:20][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]3)[CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 75710m-FluorobenzenethiolHCID 149151166-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 59378874HCID 59378874, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 6-fluoro-3,4-dihydro-2H-naphthalen-1-one (3.64 kg) and 3-fluorothiophenol (2.80 kg), in anhydrous NMP (7.7 kg) was treated with triethylamine (2.26 kg). After a mild exotherm had subsided, the mixture was heated for 20 hours at 90° C. The mixture was cooled to about 25° C. and diluted with water (30 L) and heptane (10 kg). The mixture was agitated for 12 hours and then filtered. The filter cake was washed with water and dried at 60° C. under vacuum to afford 6-(3-fluorophenylsulfanyl)-3,4-dihydro-2H-naphthalen-1-one (5.52 kg): MP=66.2-66.7° C.; MS (M+1)=273; H1 NMR (300 MHz): δ ppm (CDCl3): 2.10 (2H, m, J=6.03, 6.40 Hz), 2.62 (2H, dd, J=6.03, 5.75 Hz) 2.87 (2H, t, J=6.03), 7.03 (1H, tdd, J=1.13, 2.64, 8.29 Hz), 7.08-7.16 (2H, m), 7.22 (1H, dt, J=1.13, 8.29 Hz), 7.31 (1H, q, 8.29 Hz), 7.35 (1H, dd, J=5.65, 7.91 Hz) 7.92 (1H, d, J=7.91 Hz).

Workup

  1. temperatureThe mixture was cooled to about 25° C.
  2. filtrationfiltered
  3. washThe filter cake was washed with water
  4. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-662e939fcfa640349aff340ca3cf291b
Source dataset
uspto-grants-2016_06
Patent number
US09365494B2

Reaction notes

Loading…