Acetyl chloride → HCID 53328346, compound

HRID 1190876Notes

Reaction equation

HRID 1190876 reaction equation
C(Cl)(=O)C.[CH3:5][C:6]1[C:7]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[C:8]([CH2:15][NH:16]C(=O)OC(C)(C)C)[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1>CO>[CH3:5][C:6]1[C:7]([N:24]2[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]2)=[C:8]([CH2:15][NH2:16])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 53328344HCID 53328344, compound

Product 1

HCID 53328346HCID 53328346, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.2 mL of acetyl chloride was slowly added to 10 mL of MeOH at 0° C. The solution was stirred for 30 min at room temperature and then tert-butyl N-{[3-methyl-2-(4-methylpiperazin-1-yl)-5-nitrophenyl]methyl}carbamate (300 mg, 0.82 mmol) dissolved in 5 mL of MeOH was added. The reaction mixture was stirred for 2 h and then evaporated. The residue was dissolved in 15 mL of water and washed with diethyl ether. The aqueous layer was made alkaline (pH=10) with an aqueous NaOH 1M and extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to yield expected compound as a pale yellow oil (216 mg, quantitative yield). m/z (ESI) 265.2 [M+H]+;

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 2 h
  3. customevaporated
  4. dissolutionThe residue was dissolved in 15 mL of water
  5. washwashed with diethyl ether
  6. extractionextracted with DCM
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-64ae3cef29404b15a87e2e831fe43175
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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