Triethylamine → HCID 86702349, compound

HRID 2172539Notes

Reaction equation

HRID 2172539 reaction equation
[CH2:1]([O:3][C:4]1[CH2:9][CH2:8]/[C:7](=[CH:10]/O)/[C:6](=[N:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:5]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[SH:40]>O1CCCC1.O>[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[S:40][CH:10]=[C:7]1[C:6](=[N:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27370732,4-Difluorobenzene-1-thiolHCID 178466915HCID 178466915, compound

Product 1

HCID 86702349HCID 86702349, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

100 mg (0.39 mmol) of (Z)-4-ethoxy-2-[(4-methylphenyl)imino]cyclohex-3-en-1-ylidene methanol are dissolved in 10 ml of anhydrous tetrahydrofuran, and 325 μl (2.3 mmol) of triethylamine and 60 μl (0.78 mmol) of methanesulphonyl chloride are added at 0° C. After 30 min of stirring at 25° C., the mixture is once more cooled to 0° C., 40 μl (0.35 mmol) of 2,4-difluorobenzenethiol are added and the mixture is stirred at 25° C. for a further 30 min. The reaction mixture is diluted with water and extracted with ethyl acetate, and the organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 41 mg of N-(6-{[(2,4-difluorophenyl)sulphanyl]methylene}-3-ethoxycyclohex-2-en-1-ylidene)-4-methylaniline as an isomer mixture (ratio about 1:1).

Workup

  1. temperaturethe mixture is once more cooled to 0° C.
  2. stirringthe mixture is stirred at 25° C. for a further 30 min
  3. extractionextracted with ethyl acetate
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-9014e3243714474ba088e8c7a5de79e0
Source dataset
uspto-grants-2015_06
Patent number
US09055743B2

Reaction notes

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