4-Toluenesulfonyl chloride → HCID 10647906, compound

HRID 1417941Notes

Reaction equation

HRID 1417941 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19][OH:20])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.CO.C(Cl)(Cl)Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][O:20][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[O:16][C:15]2=[O:21])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 21584188Chloroform methanolHCID 54334011HCID 54334011, compound

Product 1

HCID 10647906HCID 10647906, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

The [3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methanol (1.465 g, 4.69 mmol) was dissolved in pyridine (15 mL) and then cooled to 0° C. (ice bath). This solution was next treated with p-toluenesulfonyl chloride (1.34 g, 7.035 mmol) and allowed to stir at 0° C. under N2 for 7 hours. At this point, the reaction was stoppered and stored in the freezer overnight (16 hours). In the morning, the reaction showed only a trace of starting material by TLC (5% MeOH/CHCl3, UV short wave). The product was precipitated by quenching the reaction mixture with ice water (100 mL). The solid was isolated by suction filtration and washed thoroughly with water. The title compound, 2.02 g (92%), was recovered as a white solid with a melting point of 141° C. and a HRMS (M+) calculated for C21H23N2O5FS2 466.1032, found 466.1036.

Workup

  1. customstored in the freezer overnight (16 hours)
  2. customThe product was precipitated
  3. customby quenching the reaction mixture with ice water (100 mL)
  4. customThe solid was isolated by suction filtration
  5. washwashed thoroughly with water
  6. customThe title compound, 2.02 g (92%), was recovered as a white solid with a melting point of 141° C.

Sources & evidence

ORD record
ord-7bf184af32f742749ea9800d33a9814f
Source dataset
uspto-grants-1999_03
Patent number
US05880118

Reaction notes

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