Sulfuric Acid → HCID 178515345, compound

HRID 1926289Notes

Reaction equation

HRID 1926289 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:8]=1[CH2:9][NH:10][C:11](=[O:17])[CH:12](OC)OC.C([O-])([O-])=O.[Na+].[Na+]>>[Cl:6][C:7]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]2[C:8]=1[CH:9]=[N:10][C:11]([OH:17])=[CH:12]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 67521110HCID 67521110, compound

Product 1

HCID 178515345HCID 178515345, compound

Conditions

Temperature
50 °C

Procedure

Sulfuric acid (18M; 0.19 mL, 3.4 mmol) was added to N-(2-chloro-3-fluorobenzyl)-2,2-dimethoxyacetamide (72.6 mg, 0.250 mmol) at ambient temperature. The mixture was stirred at 50° C. for 16 h. After cooling to rt, the mixture was poured into ice, basified with saturated Na2CO3 until pH=8, and extracted with EtOAc (3×30 ml). The extracts were washed with water (3×20 ml), brine (20 ml), dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=7.05 (s, 1H), 7.41 (dd, J=8.4 & 9.2 Hz, 1H), 7.56-7.60 (m, 1H), 9.11 (s, 1H). MS(ES+): m/z=198.14/200.02 (100/88) [MH+]. HPLC: tR=2.48 min (polar—5 min, ZQ3).

Workup

  1. temperatureAfter cooling to rt
  2. additionthe mixture was poured into ice
  3. extractionextracted with EtOAc (3×30 ml)
  4. washThe extracts were washed with water (3×20 ml), brine (20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9f5308b7df44da9a8d3e35dd2341d89
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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