Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 178471096, compound

HRID 2185191Notes

Reaction equation

HRID 2185191 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]=O)[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:26]([O:28][C:29]([CH:31]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:30])[CH3:27]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]=[CH:31][C:29]([O:28][CH2:26][CH3:27])=[O:30])[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 178519764HCID 178519764, compound

Product 1

HCID 178471096HCID 178471096, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-((3,4-dichlorophenyl)amino)-4-hydroxy-6-nitroquinazoline-8-carbaldehyde (100 mg) and ethoxycarbonylmethylene triphenylphosphorane (100 mg) in 1,2-dichloroethane (5 mL) was stirred at room temperature for 1 h. The mixture was concentrated to an oil, which was purified by preparative high pressure liquid chromatography (21.4 mm i.d.×30 cm Dynamax 300 Å C18 column; 30-90% CH3CN/H2O (+0.1% (v/v) CF3CO2H) gradient over 30 min, then to 100% CH3CN over 5 min; 15.0 mL/min flow; 1.0 min (15 mL) fractions). Fractions containing the desired product, as determined by analytical HPLC, were concentrated to afford the title compound as a crystalline yellow solid which was isolated by filtration and dried. Yield 14.2 mg. 1H NMR (300 MHz, CDCl3): δ8.79 (d, J=2.4 Hz, 1H); 8.61 (d, J=2.4 Hz, 1H), 8.20 (d, J=16.2 Hz, 1H); 7.72-7.52 (m, 3H), 6.98 (d, J=16.2 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H); 1.27 (t, J=7.2 Hz, 3H). HPLC (Method A): 8.45 min. MS (APCI+): m/z 449, 451.

Workup

  1. concentrationThe mixture was concentrated to an oil, which
  2. customwas purified by preparative high pressure liquid chromatography (21.4 mm
  3. waitto 100% CH3CN over 5 min
  4. custom1.0 min (15 mL) fractions
  5. additionFractions containing the desired product
  6. concentrationwere concentrated

Sources & evidence

ORD record
ord-472a1196b0b14aae8495e8d1babde2f7
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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