HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 555291
Notes
Print preview

Reaction equation

HRID 555291 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 669874953-Amino-4-(2-chloroethylamino)-benzoic acid methyl ester

Product 1

HCID 669873921-(2-chloroethyl)-1H-benzimidazole-5-carboxylic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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

  1. temperatureThe reaction was cooled to ambient temperature
  2. customthe solid precipitated
  3. filtrationwas filtered
  4. washwashed with water
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes