Water → HCID 178469884, compound

HRID 235948Notes

Reaction equation

HRID 235948 reaction equation
C(O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H-].[Na+].[CH2:25](I)[CH3:26].[OH2:28]>CN(C=O)C>[CH2:15]([O:28][C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][C:12]=1[C:15]1[NH:16][CH:17]=[C:18]([C:20]([O:22][CH2:25][CH3:26])=[O:21])[N:19]=1)[C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178524796HCID 178524796, compound

Product 1

HCID 178469884HCID 178469884, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

Under N2, a suspension of 16 (11.5 g, 0.039 mol), NaH (60% oil dispersion, 1.64 g, 0.041 mol) and DMF (225 ml) was heated with stirring at 60° C. After 0.5 hour, a solution of ethyliodide (6.0 g, 0.039 mol) in DMF (75 ml) was added dropwise. After the addition, the reaction was allowed to stir at room temperature overnight, then poured into H2O and extracted with EtOAc (4×). The combined organic layers were backwashed with H2O, saturated Na2CO3, saturated NaCl, dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 2% CH3OH--CHCl3 to yield 3.9 g (31%) of 17. An analytical sample was prepared by trituration with Et2O, mp 203°-5° C.

Workup

  1. temperaturewas heated
  2. additionAfter the addition
  3. stirringto stir at room temperature overnight
  4. extractionextracted with EtOAc (4×)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was chromatographed on silica gel
  9. washthe product eluted with 2% CH3OH

Sources & evidence

ORD record
ord-a68b38b57ef14c5aa50616723c11c4b4
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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