HCID 19094270, compound → HCID 18681165, compound

HRID 487182Notes

Reaction equation

HRID 487182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[NH:19][C:20](=O)[CH2:21][CH2:22][CH2:23][CH3:24])[C:13]([OH:15])=[O:14]>C(O)(=O)C.O>[CH2:21]([C:20]1[N:9]([CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:10]2[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[CH:16]=[CH:17][C:18]=2[N:19]=1)[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 19094270HCID 19094270, compound

Product 1

HCID 18681165HCID 18681165, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-[(2-chlorophenyl)methyl]amino-4-(valeryl)aminobenzoic acid (1.5 g, 4.16 mmol) in glacial acetic acid (10 mL) was refluxed for 5 hours, cooled, diluted with water (75 mL), and the crystals that separated were filtered, washed with water and dried to afford 1.33 g of crude product. Crystallization from methanol gave 1.24 g (87%) of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-benzimidazole-6-carboxylic acid; mp 238°-241° C.

Workup

  1. temperaturecooled
  2. customthe crystals that separated
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried
  6. customto afford 1.33 g of crude product
  7. customCrystallization from methanol

Sources & evidence

ORD record
ord-adda8945852345ee95534c5271bb9f89
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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