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Phenyl isocyanate → HCID 131720864, compound

HRID 399077
Notes
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Reaction equation

HRID 399077 reaction equation
[CH3:1][C:2]1([CH3:23])[CH:5]([OH:6])[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:3]1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.[C:33]1([N:39]=[C:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:1][C:2]1([CH3:23])[CH:5]([OH:6])[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:3]1[C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1.[C:33]1([NH:39][C:40](=[O:6])[O-:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 18969768HCID 18969768, compound

Product 1

HCID 131720864HCID 131720864, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 62 (150 mg) in toluene (2.3 mL) at r.t., was added diisopropylethylamine (160 μL) and phenylisocyanate (100 μL ). The mixture was refluxed for 4 hr, cooled to r.t. and diluted with EtOAc and H2O. The organic phase was washed with HCl 1N, brine, dried (MgSO4) and the solvents evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (80:20 to 60:40)) to give the title compound as a white solid, m.p. 85.5°-87° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hr
  2. washThe organic phase was washed with HCl 1N, brine
  3. dry with materialdried (MgSO4)
  4. customthe solvents evaporated
  5. customThe residue was purified by flash chromatography (silica gel; hexane/EtOAc (80:20 to 60:40))

Sources & evidence

ORD record
ord-84d3d433a4ff414ebb385aed24447486
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05817700

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes