Dibutylamine → HCID 18790602, compound

HRID 1107006Notes

Reaction equation

HRID 1107006 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:24])OC3C=CC=CC=3)=[CH:9][CH:8]=2)[N:6]=1.[CH2:25]([NH:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>CS(C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][NH:15][C:16]([N:29]([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:24])=[CH:11][CH:12]=2)[N:6]=1

Participants

4

Reactant 2

HCID 8148DibutylamineHCID 11279207HCID 11279207, compound

Product 1

HCID 18790602HCID 18790602, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound: A solution of phenyl N-{2-{4-(amino-4-thiazolyl)phenyl}ethyl}carbamate (200 mg, 0.59 mmol), prepared in the preceding section (a), and dibutylamine (76.0 mg, 0.59 mmol) in DMSO (1 mL) was stirred at room temperature for 3 d. The reaction mixture was diluted with EtOAc (30 mL) and washed with aqueous saturated NaHCO3 (2×30 mL). The aqueous layers were back extracted with EtOAc (30 mL). The combined organic extracts were dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, EtOAc:Hexane, 4:1) to give N-{2-{4-(2-amino-4-thiazolyl)phenyl}ethyl}-N',N'-dibutylurea (167 mg, 76% yield): M.p. 42-43°; 1H NMR (DMSO-d6) δ 7.70 (d, J=8.2 Hz, 2H), 7.16 (d, J=8.2 Hz, 2H), 6.99 (broad s, 2H), 6.92 (s, 1H), 6.11 (broad t, J=5.4 Hz, 1H), 3.23 (broad q, J=6.6 Hz, 2H), 3.09 (t, J=7.5 Hz, 4H), 2.70 (t, J=7.3 Hz, 2H), 1.37 (m, 4H), 1.21 (m, 4H), 0.86 (t, J=7.3 Hz, 6H); MS (FAB) m/z 375 (MH)+.

Sources & evidence

ORD record
ord-1ac4a2bda0794c5493a67ff26a1f1fdf
Source dataset
uspto-grants-2000_05
Patent number
US06057451

Reaction notes

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