Acetic Acid → HCID 53651857, compound

HRID 1684000Notes

Reaction equation

HRID 1684000 reaction equation
[CH3:1][C@H:2]([CH2:8][CH2:9][C:10](=O)[CH3:11])[CH2:3][C:4]([O:6][CH3:7])=[O:5].Cl.[Br:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)N)=[CH:17][CH:16]=1.C(O)(=O)C.C(Cl)(=O)C>C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][N:20]2[C:22]3[C:23](=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:9]([CH2:8][C@@H:2]([CH3:1])[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[C:10]2[CH3:11])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 19041688N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochlorideHCID 54169137HCID 54169137, compound

Product 1

HCID 53651857HCID 53651857, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ketone from Step 3 (92 mg, 0.3 mmol), N-(4-bromobenzyl)-N-(4-methoxyphenyl))hydrazine (52 mg, 0.3 mmol) from Example 1, Step 5, acetic acid (36 mg, 0.6 mmol) and toluene (3 mL) was stirred at room temperature for 1.5 h. The solvent was evaporated and replaced by ethanol (3 mL). Then acetyl chloride (110 mg, 5 eq) was added and the mixture was heated at 60° C. for 45 min. After evaporation of the ethanol, the mixture was chromatographed on silica gel, eluting with a 1:3 mixture of EtOAc and hexane, to afford the product as an oil which solidified (80 mg).

Workup

  1. customThe solvent was evaporated
  2. temperaturethe mixture was heated at 60° C. for 45 min
  3. customAfter evaporation of the ethanol
  4. customthe mixture was chromatographed on silica gel
  5. washeluting with a 1:3 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-4d662660a8df4417b12a9d9730731e4a
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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