Acetyl chloride → HCID 19822421, compound

HRID 1030224Notes

Reaction equation

HRID 1030224 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].Cl.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][N:23]([CH3:25])[CH3:24])=[C:11]([CH:14]=1)[CH2:12][OH:13]>C(#N)C.C(N(CC)CC)C>[C:1]([O:13][CH2:12][C:11]1[CH:14]=[C:7]([Cl:6])[CH:8]=[CH:9][C:10]=1[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][N:23]([CH3:25])[CH3:24])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 9819495133884-21-6

Product 1

HCID 19822421HCID 19822421, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of acetyl chloride (2.5 g) in 50 mL of acetonitrile was added dropwise to a solution of 9.8 g of 5-chloro-2-((2-((dimethylamino)methyl)phenyl)thio)benzyl alcohol (Example 2) in 25 mL of triethylamine and 200 mL of acetonitrile. The reaction mixture was stirred for 3 hr at room temperature, filtered and concentrated in vacuo to give a yellow oil. This oil was chromatographed on silica gel with EtOAc as the eluent. Concentration of solvents afforded 3.8 g (34% yield) of 5-chloro-2-((2-((dimethylamino)methyl)phenyl)thio)benzyl acetate as a light yellow oil. Upon standing, oil crystallized to a beige solid, m.p. 41°-44° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto give a yellow oil
  4. customThis oil was chromatographed on silica gel with EtOAc as the eluent

Sources & evidence

ORD record
ord-fa15af7a3237449c95b7680a2a3728ef
Source dataset
uspto-grants-1992_04
Patent number
US05104897

Reaction notes

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