Toluene → HCID 15538105, compound

HRID 654273Notes

Reaction equation

HRID 654273 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C(OC(=O)C1C=CC(C(O)=O)=C([N+:31]([O-:33])=[O:32])C=1)C.C([N:37]([CH2:40]C)CC)C.[NH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[C:49]1([CH3:55])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(OCC)(=O)C>[N+:31]([C:52]1[CH:53]=[CH:54][C:49]([CH3:55])=[CH:50][C:51]=1[NH:37][C:40]([NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:8])([O-:33])=[O:32]

Participants

7

Reactant 5

HCID 1140Toluene2×HCID 6115AnilineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15538104HCID 15538104, compound

Product 1

HCID 15538105HCID 15538105, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To Diphenylphosphorylazide (5.75 g) in anhydrous toluene (50 mL) at 100° C. under nitrogen was added dropwise a solution containing Ethyl-3-nitro-4-carboxybenzoate (5 gm) and triethylamine (4 mL) in anhydrous toluene (50 mL). The mixture was stirred for 1 hr followed by the addition of aniline (5 mL), and the reaction was allowed to cool to room temperature (40 min). Ethyl acetate (300 mL) was added and the solution was washed successively with 1N HCl (300 mL), water (300 mL), 1N NaOH (300 mL) and water (300 mL). The organic layer was dried and the solvent was removed in vacuo. To the resulting oil was added diethyl ether (50 mL), and the resulting solid was collected and dried yielding N-(2-Nitro-5-methylphenyl)-N'-phenyl-urea as a white solid.

Workup

  1. washthe solution was washed successively with 1N HCl (300 mL), water (300 mL), 1N NaOH (300 mL) and water (300 mL)
  2. customThe organic layer was dried
  3. customthe solvent was removed in vacuo
  4. additionTo the resulting oil was added diethyl ether (50 mL)
  5. customthe resulting solid was collected
  6. customdried

Sources & evidence

ORD record
ord-d89f6a0f84f543b6bbe405bac7bc4211
Source dataset
uspto-grants-1992_07
Patent number
US05130430

Reaction notes

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