Sodium Hydroxide → HCID 20566612, compound

HRID 1577949Notes

Reaction equation

HRID 1577949 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17]C(=O)N(C)C)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[NH2:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 129420803-[3-Chloro-4-(phenethyloxy)phenyl]-1,1-dimethylurea

Product 1

HCID 20566612HCID 20566612, compoundYield 140.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-[3-chloro-4-(phenethyloxy) phenyl]-1,1-dimethylurea (16.68 g; 0.0523 mol), n-butanol (300 ml) and 50% aqueous sodium hydroxide (50 ml) is refluxed for 1.5 hours, and then poured onto 500 ml crushed ice. The resultant mixture is extracted with ether (2×200 ml). The ether solution is washed with brine, dried over potassium carbonate and cooled in an ice bath. Dry hydrochloric acid gas is bubbled through the solution. The precipitated amine hydrochloride is collected to afford 10.46 g (0.0368 mol) of product, a white solid, m.p. 198°-204° C.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. additionpoured onto 500 ml
  3. customcrushed ice
  4. extractionThe resultant mixture is extracted with ether (2×200 ml)
  5. washThe ether solution is washed with brine
  6. dry with materialdried over potassium carbonate
  7. temperaturecooled in an ice bath
  8. customDry hydrochloric acid gas is bubbled through the solution
  9. customThe precipitated amine hydrochloride is collected

Sources & evidence

ORD record
ord-540241e1861a430aaacbcc72ce6c1643
Source dataset
uspto-grants-1981_09
Patent number
US04289903

Reaction notes

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