Sulfuric Acid → HCID 178515366, compound

HRID 1926283Notes

Reaction equation

HRID 1926283 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[CH:9](OC)OC)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:16]=[C:15]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[N:7][C:8]([OH:14])=[CH:9]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67520892HCID 67520892, compound

Product 1

HCID 178515366HCID 178515366, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

Into a RBF were added N-(4-Fluorobenzyl)-2,2-dimethoxyacetamide (1.53 g, 6.73 mmol) and sulfuric acid (18M; 3.4 mL, 61 mmol). This mixture was stirred at 85° C. for 5 min. Ice water was added and stirred; then solid NaHCO3 was added until the pH was 7-8. This was allowed to stir, then DCM was added and stirred to dissolve product. A solid precipitated out of the solution after 16 h. It was filtered off and dried in vacuo to give the title compound as yellow solid. HPLC: tR=2.07 min. (ZQ2, polar—5 min.). MS (ES+): m/z 164.24 (100) [MH+].

Workup

  1. stirringstirred
  2. stirringto stir
  3. stirringstirred
  4. dissolutionto dissolve product
  5. customA solid precipitated out of the solution after 16 h
  6. filtrationIt was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-4f7559d4ec1e4c4fbd5dad2a51033f0b
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…