Sec-Butylamine → HCID 17278316, compound

HRID 542489Notes

Reaction equation

HRID 542489 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]=[O:13])([O:3][CH3:4])=[O:2].[CH:14]([NH2:18])([CH2:16][CH3:17])[CH3:15]>O1CCCC1>[CH:14]([NH:18][C:12](=[O:13])[NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:1]([O:3][CH3:4])=[O:2])([CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 519494Methyl 2-isocyanatobenzoate2×

Product 1

HCID 17278316HCID 17278316, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

250 mg of 2-carbomethoxyphenylisocyanate (Compound II), prepared as described in Preparation I above, and 0.145 ml of sec-butylamine in dry tetrahydrofuran were stirred at room temperature for about 8 hours. The solvent was removed under reduced pressure and the resulting solid was recrystallized from ether and petroleum ether to give methyl 2-(3-sec-butylureido)-benzoate, m.p. 124°-124° C.; 'H NMR:(delta CDCl3); 0.95 (s, 3H, CH3CH2), 1,2(d, 3H, CH3CH), 1,5(m, 2H, CH3CH2), 3.8 (m, 1H, CH--N), 3.9 (s, 3H, OCH3), 4.6 (broad s, 1H, CONH--sec--Bu), 6.8, 7.2 (2 m, 2H, Ar--H), 8.0, 8.6 (2 dd, 2H, Ar--H), 10.3 (broad, 1H, ArNHCO).

Workup

  1. customas described in Preparation I above
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting solid was recrystallized from ether and petroleum ether

Sources & evidence

ORD record
ord-f52b84310dfa418bb97d8e58adf890af
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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