Hydrochloric Acid → HCID 54369742, compound

HRID 343933Notes

Reaction equation

HRID 343933 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:10]=1[CH:18]1[NH:22]C(=O)N[C:19]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[Na+].Cl>>[NH2:22][CH:18]([C:10]1[CH:11]=[CH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:9]=1[S:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:19]([OH:24])=[O:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70074605HCID 70074605, compound

Product 1

HCID 54369742HCID 54369742, compound

Conditions

Temperature
120 °C

Procedure

A solution of 5-(2-benzylthio-4-carboxyphenyl)hydantoin (0.375 g, 0.12 mmol) in 2N sodium hydroxide (6 ml, 12 mmol) was heated with stirring in a sealed reaction vessel for 20 hours at 120° C. The cooled solution was acidified wih 2N hydrochloric acid (1 ml) to pH~4 and chromatographed on ion exchange (Dowex 50×8-100). The column was eluted sequentially with water, tetrahydrofuran-water (1:1), water, then 10% pyridine in water. Fractions collected after pyridine water were combined, evaporated to dryness, redissolved in water, then freeze-dried to give the title product as an off-white solid, m.p. ~226° C.

Workup

  1. customchromatographed on ion exchange (Dowex 50×8-100)
  2. washThe column was eluted sequentially with water, tetrahydrofuran-water (1:1), water
  3. customFractions collected after pyridine water
  4. customevaporated to dryness
  5. dissolutionredissolved in water
  6. customfreeze-dried

Sources & evidence

ORD record
ord-72b9f94a4b6c4b5895680de760c3aff5
Source dataset
uspto-grants-1999_01
Patent number
US05863947

Reaction notes

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