Formic Acid → HCID 178420876, compound

HRID 532899Notes

Reaction equation

HRID 532899 reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2[O:29][CH:28]=[N:27][CH:26]=2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)=O>C(Cl)Cl>[NH:20]1[CH:24]=[C:23]([C:25]2[O:29][CH:28]=[N:27][CH:26]=2)[N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 86711346HCID 86711346, compound

Product 1

HCID 178420876HCID 178420876, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(1-trityl-1H-imidazol-4-yl)oxazole (14.5 g, 38.4 mmol) was treated with a 90% aq. solution of formic acid (90 mL) and the mixture was stirred at RT for 18 h. The mixture was then diluted with DCM, and washed with H2O and sat. aq. solution of NaHCO3. The combined aqueous layers were washed with DCM and then concentrated in vacuo. The residue obtained was placed in a Soxlet apparatus and continuously extracted with DCM for 12 h. The organic phase was then concentrated and the crude product was crystallized in DCM to give the title compound (2.68 g). UPLC-MS: MS 136.1 (M+H+); UPLC rt 0.25 min.

Workup

  1. washwashed with H2O and sat. aq. solution of NaHCO3
  2. washThe combined aqueous layers were washed with DCM
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. extractioncontinuously extracted with DCM for 12 h
  6. concentrationThe organic phase was then concentrated
  7. customthe crude product was crystallized in DCM

Sources & evidence

ORD record
ord-6aff2c6a4f1e4409ab02bf6de728d956
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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