Thionyl Chloride → 1-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

反応式

C1C=C(Cl)C(S[CH:9]([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[CH:21]2)[CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=C(Cl)C=1.[N+]([O-])(O)=O.[Cl:30]C1C=CC=CC=1CCC(O)CN1C=CN=C1.S(Cl)(Cl)=O>>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH:9]([Cl:30])[CH2:19][N:20]2[CH:21]=[CH:22][N:23]=[CH:24]2)=[CH:17][CH:16]=1

参加物

反応物 3

HCID 24386Thionyl Chloride

HCID 47471Butoconazole nitrate

HCID 690555041-[4-(Chlorophenyl)-2-hydroxy-n-butyl]-imidazole

生成物 1

HCID 124320341-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

実験手順

in the presence of sodium hydride reagent in dimethylformamide solvent. This substitution reaction takes a long time and gives the (1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole) (IV) with a poor yield (51.7%). In the next step of the butoconazole nitrate synthesis (1-[4-(chlorophenyl)-2-hydroxy-n-butyl]-imidazole) (IV) is treated with thionyl chloride (which is at once a reagent and a solvent) at 65-70° C. to yield 1-[4-(4-chlorophenyl)-2-chloro-n-butyl]-imidazole of the formula (V).

後処理

customa poor yield (51.7%)

出典と根拠

ORDレコード: ord-34ecd88d3223437283e508490c080bb9
出典データセット: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07625935B2

反応ノート

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