Glycolic Acid → HCID 67975586, compound

HRID 537846Notes

Reaction equation

HRID 537846 reaction equation
[C:1]([OH:5])(=O)[CH2:2]O.[Cl:6][C:7]1[CH:8]=[C:9]([NH2:22])[C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[CH:18]2)=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+].C(Cl)Cl>Cl.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]2[N:13]([CH2:14][CH2:15][CH2:16][N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[C:2]([CH2:1][OH:5])=[N:22][C:9]=2[CH:8]=1

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 28994099HCID 28994099, compound

Product 1

HCID 67975586HCID 67975586, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Glycolic acid (1.98 g, 26 mmol, 3 eq.) was added to a solution of 4-chloro-N1-[3-(1H-imidazol-1-yl)propyl]benzene-1,2-diamine (12, 2.18 g, 8.7 mmol) in HCl (6N, 20 mL) at room temperature. The reaction mixture was heated up until 90° C. during 16 hours. After cooling to ambient temperature the reaction mixture was diluted with 100 mL water followed by addition of NaHCO3 until the pH was approximately 7. CH2Cl2 (30 ml) was added and the organic layer was separated and the aqueous layer was further extracted with additional CH2Cl2 (20 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo and purified by flash chromatography (0 to 10% MeOH in CH2Cl2) to give {5-chloro-1-[3-(1H-imidazol-1-yl)propyl]-1H-benzimidazol-2-yl}methanol (13, 740 mg, 30%) as a white solid; LCMS m/z=291 (M+H)+

Workup

  1. temperatureAfter cooling to ambient temperature the reaction mixture
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was further extracted with additional CH2Cl2 (20 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography (0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5619fe15c03a48d89da62d8bd828e13f
Source dataset
uspto-grants-2014_10
Patent number
US08865705B2

Reaction notes

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