Trimethyl phosphite → 2-(Benzothiazol-2-yl)-5-dimethoxyphosphinylmethylpyridine

HRID 224313Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Br)=[CH:12][N:11]=1.[P:18]([O:23]C)([O:21][CH3:22])[O:19][CH3:20]>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][P:18]([O:21][CH3:22])([O:19][CH3:20])=[O:23])=[CH:12][N:11]=1

Participants

Reactant 2

HCID 8472Trimethyl phosphite

HCID 233325222-(Benzothiazol-2-yl)-5-bromomethylpyridine

Product 1

HCID 233325242-(Benzothiazol-2-yl)-5-dimethoxyphosphinylmethylpyridineYield 70%

Procedure

1.5 g (0.0049 mol) of 2-(benzothiazol-2-yl)-5-bromomethylpyridine was reacted with 3 ml of trimethyl phosphite in nitrogen gas streams at 130°-160° C. for 15 minutes. The reaction mixture was allowed to cool down to room temperature and the resulting crystals were recrystallized from ethyl acetate. By the above procedure was obtained 1.1 g (70%) of 2-(benzothiazol-2-yl)-5-dimethoxyphosphinylmethylpyridine as colorless needles, m.p. 151.5°-152.5° C.

Workup

customthe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-85607935791142ba8bc37cafdb020993
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04232010

Reaction notes

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