Ethanol → HCID 9906915, compound

HRID 1698888Notes

Reaction equation

HRID 1698888 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:8][C:9]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=[O:12])([O:3][CH3:4])=[O:2].[CH3:25]CO>>[C:1]([C:5]1[S:6][C:7]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:8][C:9]=1[NH:10][C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)=[O:12])([O:3][CH2:4][CH3:25])=[O:2]

Participants

3

Reactant 2

HCID 702EthanolHCID 9950128HCID 9950128, compound

Product 1

HCID 9906915HCID 9906915, compoundYield 59%

Procedure

A solution of Ti(OEt)4 (0.10 mL, 0.476 mmol, 11.8 equiv), N-(2-carbomethoxy-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.014 g, 0.040 mmol), and EtOH (10 mL) was heated at the reflux temp. for 36 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. The residual oil was dissolved in EtOAc and purified by flash chromatography (gradient from 10% EtOAc/hexane to 20% EtOAc/hexane) to afford N-(2-carboethoxy-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.0086 g, 59%): 1H NMR (CDCl3) δ1.30 (d, J=7.4 Hz, 3H), 1.35 (s, 9H), 2.30 (s, 3H), 4.24 (q, J=7.4 Hz, 2H), 7.11 (d, J=8.5 Hz, 2H), 7.29 (d, J=8.5 Hz, 2H), 7.30 (br s, 1H), 7.86 (s, 1H), 9.68 (s, 1H); 13C NMR (CDCl3) δ14.3, 20.8, 31.8 (3C), 35.2, 60.6, 105.1, 117.2, 121.0 (2C), 129.7 (2C), 133.8, 135.2, 145.9, 152.1, 164.2, 164.8.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe residual oil was dissolved in EtOAc
  4. custompurified by flash chromatography (gradient from 10% EtOAc/hexane to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-1e824c86708d4e88b76f47784a4fa2ae
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

Loading…