p-Chlorothiophenol → (S)-2-(4-chlorophenylsulfanyl)-1-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]ethanone

HRID 856318Notes

Reaction equation

HRID 856318 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C@:12]2([CH3:23])[O:16][C:15]3=[N:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][N:14]3[CH2:13]2)[CH2:7][CH2:6]1)=[O:4].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([SH:31])=[CH:27][CH:26]=1>>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31][CH2:2][C:3]([N:5]2[CH2:10][CH2:9][N:8]([CH2:11][C@:12]3([CH3:23])[O:16][C:15]4=[N:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][N:14]4[CH2:13]3)[CH2:7][CH2:6]2)=[O:4])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 7815p-ChlorothiophenolHCID 69481407(S)-2-chloro-1-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]ethanone

Product 1

HCID 69479631(S)-2-(4-chlorophenylsulfanyl)-1-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]ethanoneYield 20.3%

Procedure

Using a mixture of (S)-2-chloro-1-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]ethanone prepared in Example 420 (300 mg, 0.87 mmol) and 4-chlorothiophenol (190 mg, 1.32 mmol) gave (S)-2-(4-chlorophenylsulfanyl)-1-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]ethanone (80 mg, yield 20%) as a white powder in the same manner as in Example 421.

Sources & evidence

ORD record
ord-896be5ca02914bf1ba28a739c88966d2
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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