Acetic Acid → HCID 22137892, compound

HRID 1827395Notes

Reaction equation

HRID 1827395 reaction equation
[C:1](OC(=O)C)(=O)C.C(O)(=O)C.[F:12][C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.Cl>O1CCCC1.CO>[F:12][C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH3:1])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 167753144-(3-Fluoro-benzyloxy)-phenylamine

Product 1

HCID 22137892HCID 22137892, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

0.855 g (8.4 mmol) acetic anhydride is cooled to 0° and 0.475 g (10.3 mmol) acetic acid added dropwise. The reaction mixture is then heated to 55° for 2 hours. After cooling to room temperature the mixture is diluted with 0.5 ml dry tetrahydrofuran. A solution of 0.7 g (3.2 mmol) 4-(3-fluoro-benzyloxy)-phenylamine in 2 ml tetrahydrofuran is added dropwise at room temperature and the resulting mixture is stirred for 3 hours. Evaporation leaves a solid which is dissolved again in 2 ml tetrahydrofuran and cooled to 0°. 0.64 g (8.1 mmol) borane-methyl sulfide complex is slowly added under stirring and cooling. The mixture is stirred 1 h at 0° and 2 h at room temperature. After addition of 5 ml methanol, stirring is pursued for 1 h. The mixture is treated with 10 ml 1M aqueous hydrochloric acid and stirred overnight. The organic solvents are removed under vacuum and the aqueous phase adjusted to pH=10 bei addition of potassium carbonate. Extraction with diethyl ether, drying and evaporation yields 0.57 g (76%) of a colorless solid. MS: m/e=232.2 (M++H).

Workup

  1. temperatureThe reaction mixture is then heated to 55° for 2 hours
  2. customEvaporation
  3. customleaves a solid which
  4. temperaturecooled to 0°
  5. addition0.64 g (8.1 mmol) borane-methyl sulfide complex is slowly added
  6. stirringunder stirring
  7. temperaturecooling
  8. stirringThe mixture is stirred 1 h at 0° and 2 h at room temperature
  9. stirringstirring
  10. waitis pursued for 1 h
  11. stirringstirred overnight
  12. customThe organic solvents are removed under vacuum
  13. additionthe aqueous phase adjusted to pH=10 bei addition of potassium carbonate
  14. extractionExtraction with diethyl ether
  15. customdrying
  16. customevaporation

Sources & evidence

ORD record
ord-7abb05799f9d40c89e4d0caeb1bd7628
Source dataset
uspto-grants-2006_05
Patent number
US07053245B2

Reaction notes

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