Sulfuric Acid → HCID 178515344, compound

HRID 1926280Notes

Reaction equation

HRID 1926280 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[CH:8](OC)OC.S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>>[F:1][C:2]1[CH:3]=[C:4]2[C:14]([CH:8]=[C:7]([OH:13])[N:6]=[CH:5]2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67521398HCID 67521398, compound

Product 1

HCID 178515344HCID 178515344, compound

Conditions

Temperature
85 °C

Procedure

Into a RBF was added N-(3-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, and then solid NaHCO3 was carefully added until the solution was neutralized. The aqueous layer was extracted with DCM. The DCM layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. It was carried onto the next step without any further purification. HPLC: tR=2.13 min. (ZQ2, polar—5 min.). MS (ES+): m/z=164.69 (100) [MH+].

Workup

  1. stirringstirred
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe DCM layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f70fe1df581345cbb98d5254a0e539c5
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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