Methane → HCID 69059816, compound

HRID 1433153Notes

Reaction equation

HRID 1433153 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=1[OH:22])(=[O:11])[CH3:10].C([O-])([O-])=O.[Cs+].[Cs+].C>CN(C=O)C.C1(C)C=CC=CC=1>[C:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=1[O:22][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 297MethaneHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 2775185N-(4-acetyl-3-hydroxyphenyl)acetamide

Product 1

HCID 69059816HCID 69059816, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (4.84 mL, 6.97 g, 40.76 mmol) was added dropwise over 5 minutes to a mixture of give N-(4-acetyl-3-hydroxy-phenyl)-acetamide (7.50 g, 38.82 mmol) and Cs2CO3 (25.30 g, 77.64 mmol) in DMF (175 mL) at room temperature. After stirring for 18 hours, the solvent was removed in vacuo, and the residue stirred vigourously with water (200 mL) and DCM (200 mL) until dissolution was complete. The layers were separated, and the aqueous further extractede with DCM (2×200 mL). The combined organic layers were dried (MgSO4) and the solvents removed in vacuo. The residue was taken up in PhMe (150 mL) and evaporated to dryness, whereupon crystals started to form. The mixture was re-suspended in PhMe (100 mL) and refluxed for 1 hr with activated charcoal (5 g). The hot solution was filtered and allowed to cool. The product was collected by filtration to give N-(4-acetyl-3-benzyloxy-phenyl)-acetamide (5.79 g, 53%) as colourless crystals; δH (CDCl3) 7.83 (1H, m), 7.76 (1H, d, J=8.5 Hz), 7.58 (1H, br s), 7.45-7.32 (6H, m), 6.74 (1H, dd, J=8.5, 1.9 Hz), 5.15 (2H, s), 2.56 (3H, s), 2.19 (3H, s); LCMS retention time 2.33 min, M+H+ 284.3.

Workup

  1. customthe solvent was removed in vacuo
  2. stirringthe residue stirred vigourously with water (200 mL) and DCM (200 mL) until dissolution
  3. customThe layers were separated
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customevaporated to dryness, whereupon crystals
  7. customto form
  8. filtrationThe hot solution was filtered
  9. temperatureto cool
  10. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-be1f595736044005921c68125ca75866
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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