Methyl Isocyanate → 1-phenyl-2-methylaminocarbonyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

HRID 2058926Notes

Reaction equation

[C:1]1([P:7]2(=[O:16])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][N:18]=[C:19]=[O:20]>C(#N)C>[C:1]1([P:7]2(=[O:16])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][N:8]2[C:19]([NH:18][CH3:17])=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 26 °C

Procedure

A mixture of 1-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.5 g, 0.0065 mol) and methylisocyanate (1.92 g, 0.0337 mol) in 15 ml. of acetonitrile was heated with constant stirring at reflux for 16 hours. The mixture was allowed to air cool to 26° C. and was then cooled to 0° C. in an ice bath. The mixture was filtered and the precipitate washed with anhydrous ether to yield 1-phenyl-2-methylaminocarbonyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide (1.6 g, 86% yield) as a white solid having a melting point of 219°-221° C. and the following analysis:

Workup

temperatureat reflux for 16 hours
temperaturewas then cooled to 0° C. in an ice bath
filtrationThe mixture was filtered
washthe precipitate washed with anhydrous ether

Sources & evidence

ORD record: ord-5f3f46956f0a44ec96d6e871d5f27191
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04319913

Reaction notes

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