Hydrochloric Acid → HCID 178478167, compound

HRID 1946968Notes

Reaction equation

HRID 1946968 reaction equation
[Cl:1][C:2]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1.Cl>C(O)C.C([O-])([O-])=O.[Na+].[Na+]>[Cl:1][C:2]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:3]=1[O:4][CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59742755HCID 59742755, compound

Product 1

HCID 178478167HCID 178478167, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred suspension of 4-(2,3-dichloro-phenoxymethyl)-1-trityl-1H-imidazole (150 mg) at r.t. in ethanol (2 ml) under an argon atmosphere was added 2 N HCl (3 ml). The mixture was heated to reflux for 6 hours, then concentrated to leave an off-white solid. This was taken up in saturated aqueous Na2CO3 and extracted with CH2Cl2/MeOH 4:1. The combined organics were dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 4:1) to give 4-(2,3-dichloro-phenoxymethyl)-1H-imidazole (65 mg) as white solid. MS (ISP): 243.4 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. concentrationconcentrated
  4. customto leave an off-white solid
  5. extractionextracted with CH2Cl2/MeOH 4:1
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-db14175175074ed1a700cd11144db9d9
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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