Triethylamine → {2-[3-(1,1-Dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane

HRID 1457574Notes

Reaction equation

HRID 1457574 reaction equation
C[C:2]([CH3:16])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3](O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[NH2:41][C:42]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[C:48]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=1[O:44][CH2:45][O:46][CH3:47]>O.C1C=CC=CC=1>[CH3:16][C:2]([NH:36][C:39](=[O:24])[NH:41][C:42]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[C:48]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=1[O:44][CH2:45][O:46][CH3:47])([CH3:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 42657262,2-Dimethyldodecanoic acidHCID 18765846(2-Amino-4-methoxy-6-tert-butylphenoxy)methoxymethane

Product 1

HCID 22099452{2-[3-(1,1-Dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 5 g of 2,2-dimethyllauric acid, 4.72 ml of diphenylphosphorylazide (DPPA), 3.36 ml of triethylamine and 80 ml of benzene was refluxed for one hour. After cooling, a mixed solution of 5.763 g of (2-amino-4-methoxy-6-tert-butylphenoxy)methoxymethane and 20 ml of benzene was added dropwise to the above mixture. The resulting mixture was stirred at room temperature for one hour and then under reflux for 10 hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) and the product was recrystallized from hexane to give 2.89 g of {2-[3-(1,1-dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane (melting point: 83°-85° C.).

Workup

  1. temperaturewas refluxed for one hour
  2. temperatureAfter cooling
  3. temperatureunder reflux for 10 hours
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)
  9. customthe product was recrystallized from hexane

Sources & evidence

ORD record
ord-18e8b5c3d7bc4257a1aa16d682bbc4bf
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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