5-Chloro-2-methoxybenzoyl chloride → (2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-1-(5-chloro-2-methoxyphenyl)ethanone

HRID 448020Notes

Reaction equation

HRID 448020 reaction equation
[I-].[CH2:2]([N+:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:7]=1[CH3:13])[CH2:3][CH2:4][CH3:5].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:24][CH3:25])=[C:19]([CH:23]=1)[C:20](Cl)=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:20]([C:19]1[CH:23]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=1[O:24][CH3:25])=[O:21])[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 691655913-Butyl-2,4,5-trimethylthiazol-3-ium iodide

Product 1

HCID 24953558(2z)-2-(3-Butyl-4,5-dimethyl-1,3-thiazol-2(3h)-ylidene)-1-(5-chloro-2-methoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 1A (780 mg, 2.5 mmol) and 5-chloro-2-methoxy-benzoyl chloride (515 mg, 2.5 mmol) in CH2Cl2 (25 mL) under N2 atmosphere at 0° C. was added 4-dimethylaminopyridine (DMAP) (1.22 g. 10 mmol) and the mixture was allowed to warm to room temperature. The mixture was stirred for 20 hours, washed sequentially with saturated sodium bicarbonate and brine. The methylene chloride solution was dried (anhydrous MgSO4), filtered and concentrated under reduced pressure. The residue was purified by chromatography over silica gel (hexane-EtOAc 1:1 as eluent) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (t, J=7 Hz, 3H), 1.39 (sextet, J=7 Hz, 2H), 1.66 (quintet, J=7 Hz, 2H), 2.15 (s, 3H), 2.20 (s, 3H), 3.85 (s, 3H), 3.90 (t, J=7 Hz, 2H), 6.54 (s, 1H), 7.10 (d, J=9 Hz, 1H), 7.40 (dd, J=9 Hz, 3 Hz, 1H), 7.65 (d, J=3 Hz, 1H); MS (ESI) m/z 352 (M+H)+. Anal calcd for C18H22ClNO2S: C, 61.44; H, 6.30; N, 3.98. Found: C, 61.34; H, 6.17; N, 3.86.

Workup

  1. washwashed sequentially with saturated sodium bicarbonate and brine
  2. dry with materialThe methylene chloride solution was dried (anhydrous MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography over silica gel (hexane-EtOAc 1:1 as eluent)

Sources & evidence

ORD record
ord-39388975dd1a4ee1ba4edf9bb811f258
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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