Cyanamide → HCID 178474458, compound

HRID 1246442Notes

Reaction equation

Cl.[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)=[O:12])[N:10]=1)(=[O:4])[CH3:3].[N:21]#[C:22][NH2:23]>COCCO>[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:22]([NH2:23])=[NH:21])=[CH:16][CH:15]=2)=[O:12])[N:10]=1)(=[O:4])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(acetylamino)-N-(4-aminophenyl)-1,3-thiazole-4-carboxamide hydrochloride (70 mg), cyanamide (11 mg) and 2-methoxyethanol (2 ml) was stirred at 100° C. for 72 hours. The reaction mixture was concentrated in vacuo. To the residue was added ethyl acetate (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml). The precipitated solid was filtered and washed with ethyl acetate and water to give 2-(acetylamino)-N-(4-{[amino(imino)methyl]amino}phenyl)-1,3-thiazole-4-carboxamide (45 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo
additionTo the residue was added ethyl acetate (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml)
filtrationThe precipitated solid was filtered
washwashed with ethyl acetate and water

Sources & evidence

ORD record: ord-d3140f1d220e4021b7bc278a8c2e77da
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125901B2

Reaction notes

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