Triethylamine → HCID 18693127, compound

HRID 1870923Notes

Reaction equation

HRID 1870923 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2C(O)=O)=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])=CC=1.[NH2:41][NH2:42]>CN(C)C=O.C1C=CC=CC=1.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:19][C:22](=[O:31])[NH:41][NH2:42])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 9321HydrazineHCID 815682-(4-Methylphenyl)benzoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18693127HCID 18693127, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To an ice-cooling solution of (4'-methylbiphenyl-2-yl)carboxylic acid (3.0 g) and triethylamine (2.2 ml) in N,N-dimethylformamide (10 ml) was added DPPA (3.4 ml) under nitrogen atmosphere, and the mixture was stirred for 4 hours at the same temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried. The solution was added dropwise to benzene (150 ml) heated at 80° C. The mixture was then stirred for 20 minutes at the same temperature. The isocyanate solution thus prepared was added dropwise to a solution of hydrazine (2.0 ml) in benzene (50 ml) heated at 70° C. during the period of 90 minutes. The powdery product obtained by evaporating the solvent under reduced pressure was washed with ethyl acetate and dried to afford the title compound as white power (2.9 g, 85%), m.p.148-151° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. additionThe solution was added dropwise to benzene (150 ml)
  5. stirringThe mixture was then stirred for 20 minutes at the same temperature
  6. customThe isocyanate solution thus prepared
  7. temperatureheated at 70° C. during the period of 90 minutes
  8. customThe powdery product obtained
  9. customby evaporating the solvent under reduced pressure
  10. washwas washed with ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-3fdab496817048e88e0376dc012e3ae2
Source dataset
uspto-grants-2000_08
Patent number
US06100252

Reaction notes

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