Water → HCID 19771132, compound

HRID 1589870Notes

Reaction equation

HRID 1589870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[O:11].[OH-].[Na+].Cl[O-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.CO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[N:12]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=2[NH:9][C:10]1=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 295258N,N'-bis(2-methoxyphenyl)ureaHCID 23665760Sodium Hypochlorite

Product 1

HCID 19771132HCID 19771132, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A mixture of N,N'-di-(2-methoxyphenyl)-urea (6.81 g, 25 mmol) and tetra-n-butyl-ammoniumbromide (0.4 g, 1.3 mmol) in methylene chloride/methanol (1:1 , 200 ml) was at room temperature under vigorous stirring added a solution of sodium hydroxide (2 g in 10 ml water) followed by a solution of sodiumhypochlorite(55 ml, Aldrich). The mixture was stirred for 4 hours and 30 ml water was added The organic phase was washed with 10 ml 1M hydrogen chloride sol., dried and concentrated in vacuo. Upon trituration with diethyl ether dark grey crystals separated The crude product was recrystallized twice, first from ethanol and then from ethyl acetate yielding the title compound as white crystals, M.p. 246°-247° C.

Workup

  1. customwas at room temperature
  2. stirringThe mixture was stirred for 4 hours
  3. washwas washed with 10 ml 1M hydrogen chloride sol.
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customUpon trituration with diethyl ether dark grey crystals separated The crude product
  7. customwas recrystallized twice, first from ethanol

Sources & evidence

ORD record
ord-7dcec4063adf42988fb08d184ad19693
Source dataset
uspto-grants-1993_04
Patent number
US05200422

Reaction notes

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