Acetyl chloride → HCID 67285454, compound

HRID 1947428Notes

Reaction equation

HRID 1947428 reaction equation
C([CH:3]([OH:24])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:32]([O:24][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67284573HCID 67284573, compound

Product 1

HCID 67285454HCID 67285454, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution containing ethyl 3-(5-nitro-2-phenyl-1H-indol-1-yl)propan-1-ol (2.2 g; 7.4 mmol) and triethylamine (1.24 ml; 8.9 mmol) in CH2Cl2 (20 ml), acetyl chloride (0.6 ml; 8.9 mmol) was added dropwise; the reaction mixture was left under stirring at room temperature for 2 hours. Then water (20 ml) and NaHCO3 (saturated solution) were added to pH 7. The biphasic solution was transferred into a separating funnel extracted with CH2Cl2 (2×50 ml). The organic phases were combined, washed with brine (2×100 ml) and dried over Na2SO4. The solvent was removed by evaporation under reduced pressure to give 3-(5-nitro-2-phenyl-1H-indol-1-yl)propyl acetate (1.5 g), which was used without any further purification.

Workup

  1. additionwas added dropwise
  2. waitthe reaction mixture was left
  3. customThe biphasic solution was transferred into a separating funnel
  4. extractionextracted with CH2Cl2 (2×50 ml)
  5. washwashed with brine (2×100 ml)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-47caad60fcf84f95a90824d959e3b83f
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

Loading…