Acetyl chloride → HCID 22668555, compound

HRID 1883729Notes

Reaction equation

HRID 1883729 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][N:5]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[C:23](=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 8471Triethylamine2×HCID 22569398HCID 22569398, compound

Product 1

HCID 22668555HCID 22668555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.6 g of 4-(2-dimethylamino-ethylamino)-nitrobenzene (according to Gabbay et al., J. Am. Chem. Soc. 91, 5136 (1969)) are dissolved in 50 ml of methylene chloride and 5.0 ml of triethylamine are added. 1.3 ml of acetyl chloride are slowly added dropwise to this mixture at room temperature and the mixture is stirred for 2 hours at room temperature. After this time another 5.0 ml of triethylamine and 1.3 ml of acetylchloride are added and the mixture is refluxed for another 2 hours. The solvent is removed, the residue is taken up in ethyl acetate and the organic phase is extracted twice with water. After drying over MgSO4 the solvent is removed and the residue dried in vacuo.

Workup

  1. temperaturethe mixture is refluxed for another 2 hours
  2. customThe solvent is removed
  3. extractionthe organic phase is extracted twice with water
  4. dry with materialAfter drying over MgSO4 the solvent
  5. customis removed
  6. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-43b54c6d082b4b848d95077a75a21096
Source dataset
uspto-grants-2004_07
Patent number
US06762180B1

Reaction notes

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