Sodium Bicarbonate → 1-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl ester

HRID 555291Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][Cl:13])=[C:6]([NH2:14])[CH:5]=1.[C:16]([O-])(O)=O.[Na+]>C(O)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH2:12][Cl:13])[CH:16]=[N:14][C:6]=2[CH:5]=1)=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To 3-amino-4-(2-chloroethylamino)-benzoic acid methyl ester (11.0 g, 0.0482 mol) was added HCO2H (30 mL) and heated at 100° C. for 1 h. The reaction was cooled to ambient temperature and diluted with ice water (100 mL). The pH of the reaction mixture was adjusted to 7 with NaHCO3 and the solid precipitated was filtered, washed with water and dried under vacuum to get a pale green solid (9.9 g, 86%) of 1-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. MS-ESI m/z 239 (M+1).

Workup

temperatureThe reaction was cooled to ambient temperature
customthe solid precipitated
filtrationwas filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-412370c3c221467aa360239cd79ca6cd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053431B2

Reaction notes

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