Sodium Iodide → HCID 67338812, compound

HRID 1260384Notes

Reaction equation

HRID 1260384 reaction equation
C[Si](Cl)(C)C.[Cl:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](/[CH:16]=[CH:17]/[C:18]2[CH:19]=[CH:20][C:21]([O:43][CH3:44])=[C:22]([O:24][P:25](=[O:42])([O:34]CC3C=CC=CC=3)[O:26]CC3C=CC=CC=3)[CH:23]=2)=[O:15])[CH:10]=[CH:11][CH:12]=1.[Na+:45].[I-].C[O-].[Na+]>CC#N.O>[P:25]([O-:42])([O-:34])([O:24][C:22]1[CH:23]=[C:18](/[CH:17]=[CH:16]/[C:14]([NH:13][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=2)=[O:15])[CH:19]=[CH:20][C:21]=1[O:43][CH3:44])=[O:26].[Na+:45].[Na+:45]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 10942334Sodium MethoxideHCID 67338181HCID 67338181, compound

Product 1

HCID 67338812HCID 67338812, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Trimethylsilylchloride (1.68 ml, 13.3 mmol) was added dropwise to a stirred solution of phosphoric acid dibenzyl ester 5-[(E)-2-(3-chloro-phenylcarbamoyl)-vinyl]-2-methoxy-phenyl ester (1.87 g, 3.32 mmol) and NaI (1.99 g, 13.3 mmol) in dry CH3CN (40 ml). The mixture was stirred for 1 h at RT and then diluted with water and extracted with AcOEt. The organic phase was dried over sodium sulphate and evaporated in vacuo. The crude was triturated with AcOEt and Et2O, filtered and dissolved in EtOH (100 ml). NaOMe (714 mg, 13.3 mmol) was added and the resulting mixture was stirred for 2 hrs at RT. The solvent was evaporated to dryness and the residue was crystallized from water to give the title sodium (E)-5-(3-(3-chlorophenylamino)-3-oxoprop-1-enyl)-2-methoxyphenyl phosphate (1.1 g).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated in vacuo
  4. customThe crude was triturated with AcOEt and Et2O
  5. filtrationfiltered
  6. dissolutiondissolved in EtOH (100 ml)
  7. stirringthe resulting mixture was stirred for 2 hrs at RT
  8. customThe solvent was evaporated to dryness
  9. customthe residue was crystallized from water

Sources & evidence

ORD record
ord-98186bf36cf5465084983f414323905d
Source dataset
uspto-grants-2013_06
Patent number
US08470831B2

Reaction notes

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