Carbon Tetrachloride → N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

HRID 1892536Notes

Reaction equation

HRID 1892536 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)[Cl:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Cl:21][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776Triphenylphosphine2×HCID 21914951HCID 21914951, compound

Product 1

HCID 21914927N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-{2-[4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (1.383 g, 5.005 mmol) in anhydrous dichloromethane (60 ml) were added carbon tetrachloride (5.8 ml, 60 mmol) and triphenylphosphine (1.574 g, 6.000 mmol), and the mixture was stirred at room temperature for 22.5 hr. Triphenylphosphine (786.0 mg, 2.997 mmol) was added, and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:3) to give N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (1.224 g, 4.153 mmol, yield 83.0%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-fa2bb6f012fc4666a8f15435f0958bdb
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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