Dichloromethane → HCID 59481291, compound

HRID 2067652Notes

Reaction equation

HRID 2067652 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][N:6]([C:9]2[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:11]([CH3:19])[CH:10]=2)[C:5]1=[O:20].[C:21]1(C)[C:22]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1.Cl[CH2:33]Cl>N1C=CC=CC=1>[CH3:19][C:11]1[CH:10]=[C:9]([N:6]2[CH2:7][CH2:8][N:4]([CH2:3][CH2:2][O:1][S:27]([C:22]3[CH:21]=[CH:26][C:25]([CH3:33])=[CH:24][CH:23]=3)(=[O:28])=[O:29])[C:5]2=[O:20])[S:13][C:12]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 6344Dichloromethane3×HCID 8623o-Toluenesulfonyl chlorideHCID 58031585Ethyl 5-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

Product 1

HCID 59481291HCID 59481291, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of ethyl 5-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate (0.61 g, 2.04 mmol) in dichloromethane (6 mL) and pyridine (0.25 mL) at 0° C. was added toluenesulfonyl chloride in dichloromethane (1 mL). The resulting mixture was allowed to warm to ambient temperature, stirred for 18 h and diluted with dichloromethane (100 mL). The organic layer was washed sequentially with 10% aqueous hydrochloric acid (2×50 mL) and saturated aqueous sodium bicarbonate solution (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-10% ethyl acetate in dichloromethane to afford the title compound as a colorless solid in 56% yield (0.52 g): 1H NMR (300 MHz, CDCl3) δ 7.77 (d, J=8.1 Hz, 2H), 7.31 (d, J=8.1 Hz, 2H), 6.11 (s, 1H), 4.31-4.20 (m, 4H), 3.77-3.61 (m, 4H), 3.54 (t, J=4.8 Hz, 2H), 2.49 (s, 3H), 2.36 (s, 3H), 1.33 (t, J=7.1 Hz, 3H); MS (ES+) m/z 453.3 (M+1).

Workup

  1. washThe organic layer was washed sequentially with 10% aqueous hydrochloric acid (2×50 mL) and saturated aqueous sodium bicarbonate solution (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluted with 0-10% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-03e1b71230854030a332636624bb4032
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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