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

HRID 399394Notes

Reaction equation

HRID 399394 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-78653e33c0d541b391be41c803803c4b
Source dataset
uspto-grants-1998_10
Patent number
US05821239

Reaction notes

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