Sodium Hydroxide → HCID 152746712, compound

HRID 1287381Notes

Reaction equation

HRID 1287381 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][C:15](=[NH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])=[CH:7][CH:6]=1)([O-])=O.[OH-].[Na+]>O>[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH:14][C:15](=[NH:20])[CH2:16][CH2:17][CH2:18][CH3:19])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178446855HCID 178446855, compound

Product 1

HCID 152746712HCID 152746712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 30 g. of 1-(4-nitrophenyl)-3-(pentanimidoyl)urea hydrochloride (see Example 9) in 300 ml. ice-cold water was treated with 8 g. sodium hydroxide in 40 ml. water. The mixture was extracted with ether and the ethereal solution was dried over calcium sulfate and evaporated to dryness. The residue was taken up in 400 ml. absolute alcohol and hydrogenated over Raney nickel at 392 pounds pressure and at room temperature until the hydrogen uptake was complete. The catalyst was removed by filtration and the solvent was removed under reduced pressure at 50°C. to give after recrystallization successively from ether and benzene 13.5 g. of 1-(4-aminophenyl)-3-(pentanimidoyl)urea; m.p. 102°-103°C.

Workup

  1. additionice-cold water was treated with 8 g
  2. extractionThe mixture was extracted with ether
  3. dry with materialthe ethereal solution was dried over calcium sulfate
  4. customevaporated to dryness
  5. customhydrogenated over Raney nickel at 392 pounds pressure and at room temperature until the hydrogen uptake
  6. customThe catalyst was removed by filtration
  7. customthe solvent was removed under reduced pressure at 50°C.
  8. customto give
  9. customafter recrystallization successively from ether and benzene 13.5 g

Sources & evidence

ORD record
ord-a89d12226049426eb8e6c2225b824b51
Source dataset
uspto-grants-1976_10
Patent number
US03984467

Reaction notes

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