Thionyl Chloride → N-[2-(4-chloromethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

HRID 1444721Notes

Reaction equation

HRID 1444721 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:31])[CH2:13][CH:14]2[C:19](=[O:20])[NH:18][CH:17]=[CH:16][N:15]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:5][CH:4]=1.O=S(Cl)[Cl:34]>O1CCOCC1>[Cl:34][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:31])[CH2:13][CH:14]2[C:19](=[O:20])[NH:18][CH:17]=[CH:16][N:15]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68678687N-[2-(4-hydroxymethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

Product 1

HCID 68682701N-[2-(4-chloromethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N-[2-(4-hydroxymethyl-phenyl)-ethyl]-2-[3-oxo-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyrazin-2-yl]-acetamide (0.376 g, 0.85 mmol) in 1,4-dioxane (10 mL) was added SOCl2 (Aldrich, 0.25 mL, 3.4 mmol) at rt. The reaction mixture was concentrated in vacuo after 30 min. The crude product was used in next step without purification. MS (ESI): 464 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo after 30 min
  2. customThe crude product was used in next step without purification

Sources & evidence

ORD record
ord-a3e53ea43bf14617b8d9a8936f1ec533
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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