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Phenyl isocyanate → HCID 178493809, compound

HRID 1747798
Notes
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Reaction equation

HRID 1747798 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8]C.N1CCOCC1.C1(N=C=O)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[OH:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8083MorpholineHCID 137410133-Chloro-4,5-dimethoxypyridazine

Product 1

HCID 178493809HCID 178493809, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

3-Chloro-4,5-dimethoxypyridazine (17.0 g) and morpholine (59.0 mL) were stirred at 100° C. for 2 hr and the mixture was cooled to 0° C. To the reaction mixture was added phenyl isocyanate (73.8 mL) at 0° C., and the mixture was stirred at the same temperature for 30 min and diluted with ethyl acetate. The resulting N-phenylmorpholine-4-carboxamide was removed by filtration. The filtrate was concentrated and purified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate) to give the title compound (9.61 g).

Workup

  1. customThe resulting N-phenylmorpholine-4-carboxamide was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (ethyl acetate/hexane→methanol/ethyl acetate)

Sources & evidence

ORD record
ord-1ac729433b494861add832116a75e4a7
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150588B2

Reaction notes

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