Butanethiol → HCID 86599598, compound

HRID 2052754Notes

Reaction equation

HRID 2052754 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5].Cl[CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.[CH2:30]([SH:34])[CH2:31][CH2:32][CH3:33]>C1COCC1.O>[CH2:30]([S:34][CH2:17][CH2:18][S:19]([OH:21])(=[O:5])=[O:20])[CH2:31][CH2:32][CH3:33].[F:1][C:2]([F:14])([F:15])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5]

Participants

7

Reactant 4

HCID 8012ButanethiolHCID 8471Triethylamine2×HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine

Product 1

HCID 86599598HCID 86599598, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 40 mL of THF are dissolved 4.38 g (20.0 mmol) of 2,2,2-Trifluoro-1-(4-methoxyphenyl)-ethanone oxime and the solution is cooled in an ice-bath. To the solution are added successively 2-chloroethanesulfonyl chloride (2.3 mL, 22.0 mmol) and triethylamine (6.4 mL, 46.0 mmol), and the reaction solution is stirred at 0° C. for 1 h. Then, 1-butanethiol (2.4 mL, 22.0 mmol) and triethylamine (4.2 mL, 30.0 mmol) are added successively, and the reaction solution is stirred at room temperature for 0.5 h. After the reaction mixture is poured into water, the crude product is extracted with ethyl acetate twice, washed with water, dried over MgSO4 and concentrated. The residue is purified by column chromatography on silica gel with hexane—ethyl acetate (10:1 to 5:1) as an eluent to afford the product as yellow oil. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.92 (t, 3H), 1.41 (m, 2H), 1.57 (m, 2H), 2.56 (t, 2H), 2.93 (t, 2H), 3.66 (t, 2H), 3.87 (s, 3H), 7.00 (d, 2H), 7.55 (d, 2H).

Workup

  1. temperaturethe solution is cooled in an ice-bath
  2. stirringthe reaction solution is stirred at room temperature for 0.5 h
  3. extractionthe crude product is extracted with ethyl acetate twice
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography on silica gel with hexane—ethyl acetate (10:1 to 5:1) as an eluent

Sources & evidence

ORD record
ord-2258875d3b3847f69a77f9c6ff6242e4
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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