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2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine → 2,2-difluoro-6-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

HRID 638236
Notes
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Reaction equation

HRID 638236 reaction equation
[F:1][C:2]1([F:15])[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([SH:12])=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1.Cl[CH2:17][C:18]1[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=1>>[F:15][C:2]1([F:1])[O:14][C:5]2=[CH:6][C:7]3[NH:11][C:10]([S:12][CH2:17][C:18]4[C:23]([CH3:24])=[C:22]([O:25][CH3:26])[C:21]([CH3:27])=[CH:20][N:19]=4)=[N:9][C:8]=3[CH:13]=[C:4]2[O:3]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 8199922-(Chloromethyl)-4-methoxy-3,5-dimethylpyridineHCID 178506005HCID 178506005, compound

Product 1

HCID 202536992,2-difluoro-6-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazoleYield 86%

Procedure

Analogous reaction of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol with 2-chloromethyl-4-methoxy-3,5-dimethylpyridine gives 2,2-difluoro-6-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole, of m.p. 148°-149° C. (from acetonitrile), in 86% yield.

Sources & evidence

ORD record
ord-13dbcb07454c4803b58728f37b0893c4
Source dataset
uspto-grants-1985_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04560693

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes