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Cyanamide → HCID 178474458, compound

HRID 2117852
Notes
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Reaction equation

HRID 2117852 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9864CyanamideHCID 219152912-(acetylamino)-N-(4-aminophenyl)-1,3-thiazole-4-carboxamide hydrochloride

Product 1

HCID 178474458HCID 178474458, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

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

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionTo the residue was added ethyl acetate (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml)
  3. filtrationThe precipitated solid was filtered
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes