Acetyl chloride → HCID 18444305, compound

HRID 459742Notes

Reaction equation

HRID 459742 reaction equation
[CH3:1][N:2]([CH3:26])[C:3]1[CH:8]=[C:7]([CH2:9][N:10]([CH3:22])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:6]([OH:23])=[C:5]([O:24][CH3:25])[CH:4]=1.C(N(C(C)C)CC)(C)C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl>[C:36]([O:23][C:6]1[C:7]([CH2:9][N:10]([CH3:22])[CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[CH:8][C:3]([N:2]([CH3:1])[CH3:26])=[CH:4][C:5]=1[O:24][CH3:25])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 9798923BN82002 hydrochloride salt

Product 1

HCID 18444305HCID 18444305, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.1 g (0.278 mmol) of 4-(dimethylamino)-2-methoxy-6-({methyl[2-(4-nitrophenyl)ethyl]-amino}methyl)phenol (compound of Example 1) are placed in solution in 5 ml of anhydrous dichloromethane in the presence of 49 μl (0.42 mmol; 1.5 eq.) of diisopropylethylamine at 0° C. 30 μl (0.42 mmol; 1.5 eq.) of acetyl chloride are added dropwise to the solution and the medium is stirred for 1 hour at ambient temperature. Then 10 ml of dichloromethane is added to the reaction medium which is then washed with 3 times 10 ml of a saturated solution of sodium chloride. The organic phase is dried over magnesium sulphate, followed by filtering and concentrating under vacuum. The residue is purified on a silica column (eluent: AcOEt/Heptane: 2/1) in order to produce a yellow oil with a yield of 60%.

Workup

  1. washis then washed with 3 times 10 ml of a saturated solution of sodium chloride
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationby filtering
  4. concentrationconcentrating under vacuum
  5. customThe residue is purified on a silica column (eluent: AcOEt/Heptane: 2/1) in order
  6. customto produce a yellow oil with a yield of 60%

Sources & evidence

ORD record
ord-d6cf385601b8464ea23ae161a71febf3
Source dataset
uspto-grants-2007_03
Patent number
US07196084B2

Reaction notes

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