Sodium Thiosulfate → HCID 58911922, compound

HRID 874158Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5](SC)=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl[C:16]1C=CC=C(C(OO)=O)C=1.[S:26]([O-:30])([O-])(=[O:28])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[NH2:1][C:2]1[S:6][C:5]([S:26]([CH3:16])(=[O:30])=[O:28])=[N:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 5-amino-2-(methylsulfanyl)-4-phenylthiazole (302 mg, 1.36 mmol) in dichloromethane (5.0 ml) was added portionwise 3-chloroperbenzoic acid (638 mg, 77% wt, 2.9 mmol) with cooling to 0° C. The mixture was diluted with dichloromethane (3.0 ml) and after 5 min allowed to warm to ambient temperature. After 3 hr a further quantity of 3-chloroperbenzoic acid (305 mg, 77% wt, 1.4 mmol) was added portionwise. After 20 hr the mixture was treated with sodium thiosulfate (2 ml, 1.0 M), poured into saturated aqueous sodium bicarbonate and extracted three times into dichloromethane (total 100 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo to give a dark brown foam. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(methylsulfonyl)-4-phenylthiazole (90 mg, 26%).

Workup

temperatureto warm to ambient temperature
addition1.4 mmol) was added portionwise
extractionextracted three times into dichloromethane (total 100 ml)
washThe combined organic phases were washed with saturated aqueous sodium bicarbonate and brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto give a dark brown foam

Sources & evidence

ORD record: ord-e9a8b02a6f474778b10be723a6b69903
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980837B2

Reaction notes

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