Sodium Hydroxide → HCID 178501934, compound

HRID 968805Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:12]#[N:13])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[C:10]=1[CH3:11].CS[C:16]1[N:17]([C:21]([O:23][CH3:24])=[O:22])[CH2:18][CH2:19][N:20]=1.[OH-].[Na+]>C(O)(=O)C>[CH3:24][O:23][C:21]([N:17]1[CH2:18][CH2:19][NH:20][C:16]1=[N:1][C:2]1[CH:3]=[C:4]([C:12]#[N:13])[C:5]2[NH:9][CH:8]=[N:7][C:6]=2[C:10]=1[CH3:11])=[O:22]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 6-Amino-7-methyl-1H-benzimidazole-4-carbonitrile (10) (22.3 g, 0.13 mol), 4,5-dihydro-2-(methylthio)-1H-imidazole-1-carboxylic acid, methyl ester (29) (27.1 g, 0.155 mol) and glacial acetic acid (223 mL) is heated to about 85° C. for about 3 hours. The reaction mixture is allowed to cool to ambient temperature and is then concentrated in vacuo. At ambient temperature, water (223 mL) is then added to the oily residue obtained, and the pH of the resultant solution is adjusted to about 8.1 with 6N aqueous NaOH. The solids that formed are filtered, washed with water (75 mL), and dried to provide 2-(7-Cyano-4-methyl-1H-benzimidazol-5-yl-imino)-imidazolidine-1-carboxylic Acid Methyl Ester (30) (29.1 g, 75% Yield), as an off-white solid.

Workup

temperatureto cool to ambient temperature
concentrationis then concentrated in vacuo
additionAt ambient temperature, water (223 mL) is then added to the oily residue
customobtained
customThe solids that formed
filtrationare filtered
washwashed with water (75 mL)
customdried

Sources & evidence

ORD record: ord-b675a686689f4035b9997872a8d796f7
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304084B2

Reaction notes

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