Sulfuric Acid → HCID 178515369, compound

HRID 1926259Notes

Reaction equation

HRID 1926259 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]([CH:16]=1)[CH2:7][NH:8][C:9](=[O:15])[CH:10](OC)OC.OS(O)(=O)=O.OS(O)(=O)=O.O=S(=O)=O.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:17])=[C:6]2[C:16]=1[CH:10]=[C:9]([OH:15])[N:8]=[CH:7]2

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 24681Fuming sulfuric acidHCID 516892Sodium BicarbonateHCID 67520816N-(5-chloro-2-fluorobenzyl)-2,2-dimethoxyacetamide

Product 1

HCID 178515369HCID 178515369, compound

Conditions

Temperature
85 °C

Procedure

To N-(5-chloro-2-fluorobenzyl)-2,2-dimethoxyacetamide (9.00 g, 34.3 mmol) were added conc. H2SO4 (25.0 mL, 465 mmol) and oleum (30%, 25.0 mL, 394 mmol). The mixture was heated at 85° C. for 2 h. Then, the reaction mixture was cooled to RT and poured slowly into a cold aqueous satd. solution of NaHCO3 (2.0 L) in a beaker with efficient stirring (Note: frothing occurs). The solid formed was filtered off, washed with water (50 mL), and dried in vacuo to give the title compound as yellow solid. 1H NMR (CDCl3, 300 MHz): δ=6.72 (t, J=8.4 Hz, 1H), 7.15 (s, 1H), 7.43 (dd, J=8.1, 4.2 Hz), 8.80 (s, 1H), —OH not visible. MS (ES+): m/z 197.72/199.77 [MH+]. HPLC: tR=2.58 min (ZQ2, polar—5 min).

Workup

  1. temperatureThen, the reaction mixture was cooled to RT
  2. additionpoured slowly into a cold aqueous satd
  3. customThe solid formed
  4. filtrationwas filtered off
  5. washwashed with water (50 mL)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3b9a1cb9f8634e0c86800dcb40907e12
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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