Trimethyl phosphite → 1-(Benzothiazol-2-yl)-4-dimethoxyphosphinylmethylbenzene

HRID 224316Notes

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][CH: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][CH:11]=1

Participants

Reactant 2

HCID 8472Trimethyl phosphite

HCID 132767292-(4-(Bromomethyl)phenyl)benzo[d]thiazole

Product 1

HCID 135992101-(Benzothiazol-2-yl)-4-dimethoxyphosphinylmethylbenzene

Procedure

6.08 g (0.2 mol) of 4-(benzothiazol-2-yl) bromomethylbenzene was reacted with 10 ml of trimethyl phosphite in nitrogen gas at 130°-160° C. for 15 minutes. The reaction mixture was allowed to cool down to room temperature and the resulting crystals were crystallized from n-hexane to give 3.9 g (83%) of colorless flakes of 1-(benzothiazol-2-yl)-4-dimethoxyphosphinylmethylbenzene melting at 129.5°-130.5° C.

Workup

customthe resulting crystals were crystallized from n-hexane

Sources & evidence

ORD record: ord-af63bdd480874f3b9724ea1a733a4288
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04232010

Reaction notes

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