Potassium Carbonate → HCID 86758845, compound

HRID 1059883Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+:22]>CN(C)C=O>[C:5]([NH:6][C:2](=[N:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1)[S:3][CH3:4])#[N:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 2-amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole (410 mg) and potassium carbonate (415 mg) in N,N-dimethylformamide (10 ml) was added dimethyl N-cyanodithioimino-carbonate (292 mg), and the mixture was stirred at 100° C. for 1 hour. The mixture was poured into a saturated aqueous solution of ammonium chloride. Then the precipitate was collected by filtration, purified by column chromatography (silica gel 30 g, 0 to 3% methanol in dichloromethane) and recrystallized from 2-propanol to give N-cyano-N′-(4-methyl-5-(4-methylpyridin-2-yl) thiazol-2-yl)-S-methylisothiourea (0.08 g).

Workup

filtrationThen the precipitate was collected by filtration
custompurified by column chromatography (silica gel 30 g, 0 to 3% methanol in dichloromethane)
customrecrystallized from 2-propanol

Sources & evidence

ORD record: ord-2b302d11f3bf49a19892a3573b64734a
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

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