Tributylvinyltin → 2-Diethylphosphonomethyloxy-5-vinylnitrobenzene

HRID 2297032Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14](OC)=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC>CN(C=O)C.[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[CH2:7]([O:6][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:22]=[CH2:23])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-diethylphosphonomethyloxy-5-bromonitrobenzene (1 mmole, prepared as in Example 37, Step A) in DMF (5 mL) was treated with tributyl(vinyl)tin (1.2 mmole) and palladium bis(triphenylphosphine) dichloride (0.1 mmole), and the mixture was heated at 60° C. under nitrogen for 6 h. Evaporation and chromatography gave 2-diethylphosphonomethyloxy-5-vinylnitrobenzene as an oil which was subjected to Step B of Example 38, Step B of Example 36, and Step D of Example 34 to give 2-amino-7-ethyl-6-thiocyano-4-phosphonomethoxybenzothiazole (41.1). mp>167° C.(dec.). Anal. Calcd. for C11H12N3O4PS2: C:38.26; H:3.50; N:12.17. Found: C:27.87; H:3.47; N: 11.93.

Workup

customEvaporation and chromatography

Sources & evidence

ORD record: ord-57409278ac674c3fa6ce73a82affaad5
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06489476B1

Reaction notes

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