Phenylurea → HCID 14155746, compound

HRID 1252154Notes

Reaction equation

HRID 1252154 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=O)[CH2:3][CH:4]=O.S([O-])([O-])(=O)=O.[Mg+2].[C:16]1([NH:22][C:23]([NH2:25])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1([CH3:9])[CH:6]=[CH:7][N:25]([C:23]([NH:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:24])[CH:4]=[CH:3]1

Participants

6

Reactant 3

HCID 6145PhenylureaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11116082HCID 11116082, compound

Product 1

HCID 14155746HCID 14155746, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.57 g (0.036 mole) of 3,3-dimethylglutaraldehyde, 0.20 g (0.001 mole) of p-toluenesulfonic acid monohydrate and 8.64 g (0.072 mole) of anhydrous magnesium sulfate in 300 ml of dry THF was heated to reflux under nitrogen. 4.89 g (0.036 mole) of phenylurea in 125 ml of dry THF was added over a period of 1 hour. Refluxing was continued for an additional 40 minutes before the reaction mixture was filtered and the filtrate evaporated in vacuo to yield 8.23 g of a brown oil. The crude product was purified by silica gel column chromatography on 410 g of CC-7 silica gel eluting with a 7.5% ethyl acetate/hexane solution. The eluate was evaporated in vacuo to yield 4.74 g of the title compound, a white solid, mp 128°-130° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureRefluxing
  4. filtrationwas filtered
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-250aeaf7a8d04946a6ae6a01b0291296
Source dataset
uspto-grants-1988_05
Patent number
US04742068

Reaction notes

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