HCID 21930302, compound → HCID 21930292, compound

HRID 1243659Notes

Reaction equation

HRID 1243659 reaction equation
ClCC([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[OH:18])=O>C(O)C.Cl>[NH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]([F:16])([F:17])[F:15])=[CH:9][C:8]=1[OH:18]

Participants

4

Reactant 1

HCID 21930302HCID 21930302, compound

Product 1

HCID 21930292HCID 21930292, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

2-Chloro-N-(2-hydroxy-4-trifluoromethoxy-benzyl)-acetamide (9.9 g, 37.4 mmol) was dissolved in a mixture of ethanol (100 mL)/aqueous HCl (12 M, 50 mL). The mixture was refluxed for ˜6 hours. The solvent was removed by rotary evaporation and the residue was azeotropically dried by dissolution in ethyl acetate followed by rotary evaporation (6×150 mL). The resulting solid was suspended in ethyl acetate (100 mL), collected by filtration and dried at 65° C. in a vacuum oven overnight. Recovery: 8.68 g (95.3% yield). M/Z (−HCl) of [M−H]−=208. 1H NMR (D2O) δ=7.26–7.22 (1H, sd), 6.76–6.75 (2H, br), 4.07 (2H, s).

Workup

  1. temperatureThe mixture was refluxed for ˜6 hours
  2. customThe solvent was removed by rotary evaporation
  3. dry with materialthe residue was azeotropically dried by dissolution in ethyl acetate
  4. customfollowed by rotary evaporation (6×150 mL)
  5. filtrationcollected by filtration
  6. customdried at 65° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-49f9646fd42d466cb5b46f385cc72556
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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