Water → 5-Dimethylamino-naphthalene-1-sulfonic acid 2,2,2-trifluoro-1-(4-methyldisulfanyl-phenyl)-ethyl ester

HRID 522342Notes

Reaction equation

HRID 522342 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][S:12][CH3:13])=[CH:7][CH:6]=1)[OH:4].[S:16](Cl)([C:19]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:24]([N:25]([CH3:27])[CH3:26])[C:23]=2[CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17].C1N2CCN(CC2)C1.O>C(Cl)Cl>[F:15][C:2]([F:1])([F:14])[CH:3]([O:4][S:16]([C:19]1[C:31]2[C:23](=[C:24]([N:25]([CH3:27])[CH3:26])[CH:28]=[CH:29][CH:30]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:5]1[CH:6]=[CH:7][C:8]([S:11][S:12][CH3:13])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 11801Dansyl chlorideHCID 90402522Trifluoro-1-(4-methyldisulfanyl-phenyl)-ethanol

Product 1

HCID 863018255-Dimethylamino-naphthalene-1-sulfonic acid 2,2,2-trifluoro-1-(4-methyldisulfanyl-phenyl)-ethyl esterYield 28.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,2,2-Trifluoro-1-(4-methyldisulfanyl-phenyl)-ethanol (6) (12 mg, 0.047 mmol) and dansyl chloride (15 mg, 0.057 mmol) were dissolved in dry CH2Cl2 (0.2 mL). A solution of DABCO (63 mg, 0.56 mmol) dissolved in dry CH2Cl2 (0.1 mL) was added dropwise to the above solution. After 4 hours at room temperature, the reaction was poured into H2O (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with H2O (3×30 mL), followed by brine (1×30 mL) and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation. Flash chromatography on silica gel using 0-15% acetone/hexanes to yield Compound 1 as a yellow solid (6.5 mg, 28%). 1H NMR (400 MHz, CDCl3): δ 8.46 (d, J=8.5 Hz, 1H), 8.2 (d, J=8.7 Hz, 1H), 8.07 (d, J=7.3 Hz, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 7.16 (d, J=7.2 Hz, 1H), 7.13 (d, J=8.4 Hz, 2H), 7.03 (d, J=8.3 Hz, 2H), 5.59 (q, J=6.3 Hz, 1H), 2.84 (s, 6H), 2.37 (s, 3H); 19F NMR (376 MHz, CDCl3): δ −76.3 (d, J=6.3 Hz). HRMS calc'd for C21H21F3NO3S3: 488.0636. found: 488.0647.

Workup

  1. additionwas added dropwise to the above solution
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic phases were washed with H2O (3×30 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationThe organic phase was collected by filtration
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-432d1b32fb3743e4a044dff8a6dd365a
Source dataset
uspto-grants-2016_05
Patent number
US09329185B2

Reaction notes

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