4-Chlorobenzyl mercaptan → HCID 69515471, compound

HRID 1178706Notes

Reaction equation

HRID 1178706 reaction equation
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][SH:14])=[CH:9][CH:8]=1.[CH3:15][O:16][C:17]([C:19]1[C:20](S(C)(=O)=O)=[N:21][S:22][C:23]=1[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18]>C1COCC1>[CH3:15][O:16][C:17]([C:19]1[C:20]([S:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)=[N:21][S:22][C:23]=1[NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18]

Participants

5

Reactant 3

HCID 804094-Chlorobenzyl mercaptanHCID 69515138HCID 69515138, compoundHCID 178418339Butyllithium

Product 1

HCID 69515471HCID 69515471, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of n-BuLi (2.5M, 11.5 mL, 28.8 mmol) in THF (20 mL) at 0° C. is added (4-Chloro-phenyl)-methanethiol (4 mL, 30 mmol) dropwise over 15 min. After 1 hr., a solution of 18 (2 g, 6 mmol) in THF (15 mL) is added. The reaction is then stirred at 0° C. for 1 hour and 2 hrs. at room temperature. The reaction was then quenched with water and extracted with EtOAc (3×50 mL). The combined organics are then washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (3% EtOAc/hexane) provides 19 (1.98 g, 80%) as a white solid. 1H NMR (CDCl3): δ 10.00 (1H, br. s), 7.29 (2H, d, J=8.4 Hz), 7.25 (2H, d, J=8.4 Hz), 4.36 (2H, s), 3.89 (3H, s), 1.53 (9H, s).

Workup

  1. customat room temperature
  2. customThe reaction was then quenched with water
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe combined organics are then washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c790eee35dc4a13b61a2fc1a967394b
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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