Toluene → HCID 67664036, compound

HRID 1455895Notes

Reaction equation

HRID 1455895 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](C=O)=[CH:16]2)=[O:11].[CH3:24][O:25][C:26](=[O:47])[CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:48]1(C)C=CC=CC=1>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([NH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH:48]=[CH:27][C:26]([O:25][CH3:24])=[O:47])=[CH:16]2)=[O:11]

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 22105402HCID 22105402, compound

Product 1

HCID 67664036HCID 67664036, compoundYield 66%

Procedure

21 (100 mg, 0.33 mmol) was added to a solution of methyl(triphenylphosphoranylidene)acetate (120 mg, 0.36 mmol) in toluene (30 mL) and the reaction mixture was heated to reflux for 4 days. The solvent was removed after cooled to room temperature. The product was crystallized in a solution of acetone and ether. The mother liquid was then purified by flush column chromatography eluting with ethyl acetate and hexane (1/2, v/v). A total of 78 mg (66% yield) of yellow solid 22 was obtained. mp: 259°-260° C. 1H NMR (DMSO-d6, ppm): 11.57 (s, 1 H, NH), 10.38 (s, 1 H, NH), 8.07-7.35 (m, 9 H, Ar--H, CH=CH), 6.93 (s, 1 H, Ar--H), 6.57-6.53 (d, 1 H, J=15.8 Hz, CH=CH), 3.74 (s, 3 H, CH3). Anal. (C21H16N2 O4), C, H, N.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 4 days
  3. customThe solvent was removed
  4. customThe product was crystallized in a solution of acetone and ether
  5. customThe mother liquid was then purified
  6. customby flush column chromatography
  7. washeluting with ethyl acetate and hexane (1/2

Sources & evidence

ORD record
ord-754737bbb63b477a94bf99425a7e81aa
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

Loading…