Cyanamide → HCID 178474458, compound

HRID 2117852Notes

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-a83fd9b105704aaaa0fd707acc4b70ea
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442715B2

Reaction notes

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