Acetic Anhydride → N-[6-(2,6-Dichlorophenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylidene]-acetamide

HRID 3200Notes

Reaction equation

HRID 3200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[NH:21])[N:19]([CH2:22][CH3:23])[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:20](=[N:21][C:24](=[O:26])[CH3:25])[N:19]([CH2:22][CH3:23])[C:12]2[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 105708306-(2,6-dichlorophenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine

Product 1

HCID 10549360N-[6-(2,6-Dichlorophenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylidene]-acetamide

Procedure

A mixture of 2.70 g (7.40 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine of Example 65 and 15 mL of acetic anhydride was heated with stirring to the boiling point. The resulting solution was heated at reflux for 5 minutes and concentrated at reduced pressure to ca. 8 mL volume. The solution was cooled and ether (8 mL) was added. The well-defined crystals that separated were filtered and washed with 5 mL of ether and 10 mL of petroleum ether; wt 2.68 g; mp 175°-177° C.

Workup

  1. temperaturewas heated
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 5 minutes
  4. concentrationconcentrated at reduced pressure to ca. 8 mL volume
  5. temperatureThe solution was cooled
  6. additionether (8 mL) was added
  7. customThe well-defined crystals that separated
  8. filtrationwere filtered
  9. washwashed with 5 mL of ether and 10 mL of petroleum ether

Sources & evidence

ORD record
ord-8675cbe68b9f48d288dee7a6e5c59cad
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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