Hydrochloric Acid → HCID 178514079, compound

HRID 1858510Notes

Reaction equation

HRID 1858510 reaction equation
[NH2:1][C:2]1[S:6][C:5]([SH:7])=[N:4][CH:3]=1.[O-:8][C:9]#[N:10].[Na+].O1CCCC1.Cl>O.C(O)(=O)C.C(OCC)(=O)C>[NH:1]([C:2]1[S:6][C:5]([SH:7])=[N:4][CH:3]=1)[C:9]([NH2:10])=[O:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 517096Sodium CyanateHCID 178508044HCID 178508044, compound

Product 1

HCID 178514079HCID 178514079, compoundYield 6.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-amino-2-mercaptothiazole (6.61 g) in water (34 ml) and acetic acid (17 ml) was added a solution of sodium cyanate (6.50 g) in water (55 ml) at 35° C. After stirring at the same temperature for 2 hours, the solution was poured into a mixture of water, tetrahydrofuran and ethyl acetate, and adjusted to pH 3.0 with 1N-hydrochloric acid. The separated organic layer was washed with saturated sodium chloride solution (×2), dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give 5-ureido-2-mercaptothiazole (577 mg).

Workup

  1. washThe separated organic layer was washed with saturated sodium chloride solution (×2)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57030804e0d94358b6b9c527ea808870
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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