Hydrochloric Acid → HCID 86591039, compound

HRID 1592002Notes

Reaction equation

HRID 1592002 reaction equation
C([O:3][CH:4](OCC)[C:5]1[S:9][C:8]([CH2:10][N:11]2[S:15](=[O:17])(=[O:16])[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[O:27][CH3:28])[C:13](=[O:29])[CH2:12]2)=[CH:7][CH:6]=1)C.Cl>C1COCC1>[CH3:28][O:27][C:20]1[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:19]=1[CH2:18][N:14]1[S:15](=[O:17])(=[O:16])[N:11]([CH2:10][C:8]2[S:9][C:5]([CH:4]=[O:3])=[CH:6][CH:7]=2)[CH2:12][C:13]1=[O:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67138199HCID 67138199, compound

Product 1

HCID 86591039HCID 86591039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title A compound, 5-(5-diethoxymethyl-thiophen-2-ylmethyl)-2-(2,4-dimethoxy-benzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (3.91 g, 8.1 mmol) is dissolved in THF (100 mL) and 6N aqueous HCl (2.7 mL) is added. The mixture is stirred for 2 h and the solvent is evaporated. The residue is partitioned between EtOAc and saturated aqueous NaHCO3 solution. The organic layer is dried over anhydrous MgSO4 and concentrated to dryness. The residue is triturated from Et2O to afford 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carbaldehyde as a yellow solid.

Workup

  1. customthe solvent is evaporated
  2. customThe residue is partitioned between EtOAc and saturated aqueous NaHCO3 solution
  3. dry with materialThe organic layer is dried over anhydrous MgSO4
  4. concentrationconcentrated to dryness
  5. customThe residue is triturated from Et2O

Sources & evidence

ORD record
ord-7a311c3dfa8243198292357950a151a4
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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