Water → HCID 22675442, compound

HRID 1005970Notes

Reaction equation

HRID 1005970 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14]1[NH:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:33])[CH2:31][CH3:32].O>CC(N(C)C)=O.C(#N)C.CCCCCC>[C:30]([N:18]1[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]=[C:14]1[S:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)(=[O:33])[CH2:31][CH3:32]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 9796852HCID 9796852, compound

Product 1

HCID 22675442HCID 22675442, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 31374DimethylacetamideSolvent

Procedure

0.2 g of (Compound 1) was dissolved in 0.8 ml of dimethylacetamide and 1.6 ml of acetonitrile, added with 0.14 ml of triethylamine and then added with 74 mg of propionyl chloride at 50° C. After 30 minutes, the reaction mixture was cooled and added with water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by using a silica gel column (ethyl acetate:methylene chloride=1:5) and crystallized from ethyl acetate:hexane to obtain 0.17 g of the title compound (yield: 72%).

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified
  7. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c943c82fa1e6452a81adc476cb71fdac
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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