Trimethyl orthoformate → HCID 178519707, compound

HRID 547634Notes

Reaction equation

HRID 547634 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2OCC[O:9]2)[CH:5]=[CH:4][C:3]=1[O:13][C:14]1[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=1.[CH:22](OC)(OC)OC>>[NH:20]1[C:17]2[CH:18]=[CH:19][C:14]([O:13][C:3]3[CH:4]=[CH:5][C:6]([CH:8]=[O:9])=[CH:7][C:2]=3[Cl:1])=[CH:15][C:16]=2[N:21]=[CH:22]1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 57585835HCID 57585835, compound

Product 1

HCID 178519707HCID 178519707, compound

Procedure

Crude 4-{[2-chloro-4-(1,3-dioxolan-2-yl)phenyl]oxy}-1,2-benzenediamine was heated to reflux in 5 mL of trimethyl orthoformate for 2 hours. The reaction mixture was then concentrated and purified by preparative HPLC, with conconiment loss of the dioxolane protecting group. The HPLC fractions were combined and diluted with 1N NaOH, extracted with ethyl acetate, dried over MgSO4 and concentrated to give 4-(1H-benzimidazol-5-yloxy)-3-chlorobenzaldehyde. (M+1) 272.9, 1.65 min (LC/MS method B)

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by preparative HPLC, with conconiment loss of the dioxolane protecting group
  3. additiondiluted with 1N NaOH
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c44c00e6857643d186d02f653b14b2e1
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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