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

HRID 2058926
Notes
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Reaction equation

HRID 2058926 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 130375021-phenyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxide

Product 1

HCID 130375281-phenyl-2-methylaminocarbonyl-2,3-dihydro-1H-2,1-benzazaphosphole-1-oxideYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. temperatureat reflux for 16 hours
  2. temperaturewas then cooled to 0° C. in an ice bath
  3. filtrationThe mixture was filtered
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes