Water → HCID 5282563, compound

HRID 379580Notes

Reaction equation

HRID 379580 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].O.C(=O)(O)[O-].[Na+]>C(O)(=O)C(C)C>[CH3:6][CH:7]([CH3:14])[CH2:8][NH:3][C:4]1[S:5][CH:6]=[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2×HCID 52825623,4-Diethyl 2-aMinothiophene-3,4-dicarboxylate

Product 1

HCID 5282563HCID 5282563, compoundYield 172.4%

Reagents, catalysts & solvents 1

HCID 6590Isobutyric AcidSolvent

Procedure

Sodium borohydride (18 g) was added portionwise over 5 hours to a stirred suspension of diethyl 2-aminothiophene-3,4-dicarboxyate (33 g) in isobutyric acid (300 ml) at room temperature. The mixture was stirred for 16 hours then further sodium borohydride (4 g) was added and stirring was continued for 5 hours. Water (1.51) was added, the mixture was neutralised by addition of solid sodium bicarbonate and then extracted with ether (3×500 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated to give the subtitle compound (35 g) as a solid.

Workup

  1. stirringstirring
  2. waitwas continued for 5 hours
  3. extractionextracted with ether (3×500 ml)
  4. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-95cb73f5693144e38dd0ae18fd3a6c07
Source dataset
uspto-grants-2001_10
Patent number
US06300334B1

Reaction notes

Loading…