Acetyl chloride → HCID 59676138, compound

HRID 1880464Notes

Reaction equation

HRID 1880464 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]1[C:14]3[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=3[O:12][CH2:11][C:10]2=1.CCN(CC)CC>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([C:1](=[O:3])[CH3:2])[C:15]1[C:14]3[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=3[O:12][CH2:11][C:10]2=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 619571HCID 619571, compound

Product 1

HCID 59676138HCID 59676138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.064 mL, 0.896 mmoL) in CH2Cl2 (2 mL) was treated with 8-methoxy-6,11-dihydro-5-oxa-11-aza-benzo[a]fluorene (150 mg, 0.598 mmoL) followed by Et3N (0.896 mmol., 0.125 mL) at 0° C. The reaction mixture was then slowly warmed to room temperature over 2 hours. The reaction mixture was then partitioned between CH2Cl2 and saturated NaHCO3. The aqueous phase was extracted two times with CH2Cl2. The organic layers from the two extractions were then combined, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material was then purified by column chromatography (silica gel, hexanes:EtOAc 3:1 as eluent) to yield the title compound as a pale solid.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and saturated NaHCO3
  2. extractionThe aqueous phase was extracted two times with CH2Cl2
  3. extractionThe organic layers from the two extractions
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe crude material was then purified by column chromatography (silica gel, hexanes:EtOAc 3:1 as eluent)

Sources & evidence

ORD record
ord-53ff044c0c65436c81ccbd335ecba86a
Source dataset
uspto-grants-2012_11
Patent number
US08318766B2

Reaction notes

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