Sulfuric Acid → HCID 178515370, compound

HRID 1926268Notes

Reaction equation

HRID 1926268 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:8]([F:23])=[CH:9][C:10]([F:22])=[C:11]([CH:21]=1)[CH2:12][NH:13][C:14](=[O:20])[CH:15](OC)OC.[OH-].[Na+]>>[Cl:6][C:7]1[C:8]([F:23])=[CH:9][C:10]([F:22])=[C:11]2[C:21]=1[CH:15]=[C:14]([OH:20])[N:13]=[CH:12]2

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67520609N-(5-chloro-2,4-difluorobenzyl)-2,2-dimethoxyacetamide

Product 1

HCID 178515370HCID 178515370, compound

Conditions

Temperature
90 °C

Procedure

Sulfuric acid (18 M; 2.0 mL, 36 mmol.) was added to N-(5-chloro-2,4-difluorobenzyl)-2,2-dimethoxyacetamide (708 mg, 2.53 mmol) at rt. The solution was stirred at 90° C. overnight. After that time, the mixture was poured into ice and basified with NaOH (10 N) until pH=6-7 forming a solid. The solid was filtered off, washed with water, and dried in vacuo to give the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=6.94 (t, J=9.2 Hz, 1H), 7.48 (s, 1H), 9.04 (s, 1H). MS(ES+): m/z=215.47/217.76 (45/100) [MH+]. HPLC: tR=2.67 min (polar—5 min, ZQ3).

Workup

  1. additionAfter that time, the mixture was poured into ice
  2. customforming a solid
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-029b3c69756648dca1bc0895bea02288
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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