Triethylamine → 1-Hydroxy-1-(1-ethylpropyl)-3-(2-phenoxyphenyl)urea

HRID 976648Notes

Reaction equation

HRID 976648 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[CH2:41]([CH:43]([NH:46][OH:47])[CH2:44][CH3:45])[CH3:42]>C1(C)C=CC=CC=1>[OH:47][N:46]([CH:43]([CH2:44][CH3:45])[CH2:41][CH3:42])[C:22]([NH:19][C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 752372-Phenoxybenzoic acidHCID 199401P,P-Diphenylphosphinic azideHCID 19073513N-(pentan-3-yl)hydroxylamine

Product 1

HCID 199673731-Hydroxy-1-(1-ethylpropyl)-3-(2-phenoxyphenyl)ureaYield 59.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-phenoxybenzoic acid (2.63 g, 12.3 mmole), triethylamine (1.8 mL, 13 mmole) and diphenylphosphoryl azide (2.9 mL, 13.5 mmole) in toluene (50 mL) was heated at 95° C. for 2 hours. The reaction was cooled to ambient temperature and N-(1-ethylpropyl)hydroxylamine (1.9 g, 18.4 mmole) was added as a solid. The reaction was maintained overnight then concentrated under vacuum to provide the crude product as a yellow oil. The residue was partitioned between diethyl ether (100 mL) and water (100 ml). The fractions were separated and the aqueous fraction was extracted with additional portions of diethyl ether (3×50 mL). The combined organic fractions were dried over sodium sulfate, filtered and concentrated. The residue was recrystallized from hexanes.backslash.ethyl acetate to provide 2.3 g of the desired product as a white crystalline solid, m.p. 141.2°-141.8° C. Analysis: Calculated for C18H22N2O3 : %C, 68.77; %H, 7.05; %N, 8.91; Found: %C, 68.23; %H, 6.8; %N, 8.89.

Workup

  1. temperatureThe reaction was maintained overnight
  2. concentrationthen concentrated under vacuum
  3. customto provide the crude product as a yellow oil
  4. customThe residue was partitioned between diethyl ether (100 mL) and water (100 ml)
  5. customThe fractions were separated
  6. extractionthe aqueous fraction was extracted with additional portions of diethyl ether (3×50 mL)
  7. dry with materialThe combined organic fractions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-e1e2962eb19c4d938b43a9252c970507
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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