O-Phenylenediamine → HCID 67996031, compound

HRID 921036Notes

Reaction equation

HRID 921036 reaction equation
OOS([O-])=O.[K+].[C:7]([C:11]1[N:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][N:12]=1)([CH3:10])([CH3:9])[CH3:8].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:7]([C:11]1[N:16]=[CH:15][C:14]([C:17]2[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:26]=2)=[CH:13][N:12]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 112059602-tert-butylpyrimidine-5-carbaldehydeHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 67996031HCID 67996031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

16.9 g (55 mmol) of oxone [70693-62-8] are added in portions with stirring at 10° C. to a solution of 16.4 g (100 mmol) of 2-tert-butylpyrimidine-5-carboxaldehyde [104461-06-5] and 11.9 g (110 mmol) of 1,2-diaminobenzene in a mixture of 100 ml of DMF and 3 ml of water, and the mixture is subsequently stirred at room temperature until conversion of the aldehyde is complete (about 2 h). The reaction mixture is stirred into a solution of 40 g of potassium carbonate solution in 2000 ml of water, stirred for a further 15 min., the solid formed is filtered off with suction, washed three times with 100 ml of water each time and dried in vacuo. The solid is dissolved in about 50 ml of hot ethyl acetate, and, during cooling, diethyl ether is added until slightly cloudy, the mixture is stirred for a further 12 h, the crystals are filtered off with suction, washed once with 50 ml of diethyl ether and dried in vacuo. Yield: 16.6 g (66 mmol), 66%. Purity: >95% according to 1H-NMR.

Workup

  1. custom(about 2 h)
  2. customthe solid formed
  3. filtrationis filtered off with suction
  4. washwashed three times with 100 ml of water each time
  5. customdried in vacuo
  6. dissolutionThe solid is dissolved in about 50 ml of hot ethyl acetate
  7. temperatureduring cooling
  8. additiondiethyl ether is added until slightly cloudy
  9. stirringthe mixture is stirred for a further 12 h
  10. filtrationthe crystals are filtered off with suction
  11. washwashed once with 50 ml of diethyl ether
  12. customdried in vacuo

Sources & evidence

ORD record
ord-485a09f794084eaca2bb3f9d7b66922e
Source dataset
uspto-grants-2016_03
Patent number
US09273080B2

Reaction notes

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