Water → HCID 15410541, compound

HRID 1066951Notes

Reaction equation

HRID 1066951 reaction equation
[OH:1][C:2]([C:15]([F:18])([F:17])[F:16])([CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[C:3]([OH:5])=O.S(Cl)(Cl)=O.[NH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[O:30])[O:28][CH2:27]2.O>CC(N(C)C)=O>[OH:1][C:2]([C:15]([F:18])([F:17])[F:16])([CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:8])[C:3]([NH:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[O:30])[O:28][CH2:27]2)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 7206695-AminophthalideHCID 15410540HCID 15410540, compound

Product 1

HCID 15410541HCID 15410541, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-15 °C

Procedure

500 mg of 2-hydroxy-4-phenyl-2-trifluoromethyl-valeric acid (Eur. Appl. 0 253 500 (Imperial Chemical Industries)) in 10 ml of dimethylacetamide is mixed at −15° C. with 0.14 ml of thionyl chloride. After 3 hours of stirring at −15° C., 600 mg of 5-aminophthalide (test) is added. The solution is stirred for 2 hours at −15° C. and then left for 18 hours at room temperature, then mixed with water and extracted with ethyl acetate. The ethyl acetate phase is dried (Na2SO4) and concentrated by evaporation. The residue is stirred with diethyl ether and suctioned off. 290 mg of 5-(2-hydroxy-4-phenyl-2-trifluoromethyl-valeroylamino)-phthalide, melting point 166-168° C., is obtained.

Workup

  1. stirringThe solution is stirred for 2 hours at −15° C.
  2. waitleft for 18 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase is dried (Na2SO4)
  5. concentrationconcentrated by evaporation
  6. stirringThe residue is stirred with diethyl ether

Sources & evidence

ORD record
ord-2be0728612f541fd8ef57ff3530c2d5c
Source dataset
uspto-grants-2001_06
Patent number
US06245804B1

Reaction notes

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