Phenyl isocyanate → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol phenylcarbamate

HRID 361334

Reaction equation

HRID 361334 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1>[C:13]1([NH:19][C:20]([O:12][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:6]=2[N:5]=[CH:4][N:2]([CH3:1])[CH3:3])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Product 1

HCID 677490644-[[(Dimethylamino)methylene]amino]-3-pyridinol phenylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a warm solution of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (3.0 g) in dry tetrahydrofuran (60 mL) was added phenyl isocyanate (2.05 mL). The reaction mixture was stirred at room temperature for 1.5 hours and filtered. The solid was washed with dry diethyl ether, air dried, and dried under high vacuum and refluxing ethanol for 4 hours to yield 4.19 g of solid, m.p. 151° C.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with dry diethyl ether, air
  3. customdried
  4. customdried under high vacuum
  5. temperaturerefluxing ethanol for 4 hours

Sources & evidence

ORD record
ord-5346322bd6644f4ba5dfc813f96a7685
Source dataset
uspto-grants-1999_02
Patent number
US05866565

Linked notes

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