Tetrahydrofuran → HCID 85074614, compound

HRID 1058640Notes

Reaction equation

HRID 1058640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].O[C:13](=[C:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1C[O:30]CC1>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:30][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:13]=[C:20]1[S:24][C:23](=[O:25])[NH:22][C:21]1=[O:26])=[O:6]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 178518521HCID 178518521, compound

Product 1

HCID 85074614HCID 85074614, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,4-dichlorobenzoylchloride in THF was slowly added to a solution of 5-(hydroxybenzylidene)thiazolidine-2,4-dione (1.5 eq.) and TEA (1.5 eq.) in THF. The resulting reaction was stirred for 1-2 h at which time the solid was filtered and filtrate was concentrated under reduced pressure to yield light yellow solid. The solid was dissolved in EtOAc followed by washing with sat. aq. K2CO3. The organic phase was separated, and dried over Na2SO4 followed by concentration under reduced pressure to yield pure compound.

Workup

  1. customThe resulting reaction
  2. filtrationwas filtered
  3. concentrationfiltrate was concentrated under reduced pressure
  4. customto yield light yellow solid
  5. washby washing with sat. aq. K2CO3
  6. customThe organic phase was separated
  7. dry with materialdried over Na2SO4
  8. concentrationfollowed by concentration under reduced pressure
  9. customto yield pure compound

Sources & evidence

ORD record
ord-d9b56e205045484089bed1e699accb2c
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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