Benzoyl chloride → HCID 54148715, compound

HRID 246809Notes

Reaction equation

HRID 246809 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CN=CC=1.[CH2:17]([O:19][N:20]=[C:21]([C:25]1[C:26](=[O:39])[CH2:27][CH:28]([C:32]2[S:33][C:34]([CH3:38])=[C:35]([CH3:37])[N:36]=2)[CH2:29][C:30]=1[OH:31])[CH2:22][CH2:23][CH3:24])[CH3:18]>ClCCl>[CH2:17]([O:19][N:20]=[C:21]([C:25]1[C:26](=[O:39])[CH2:27][CH:28]([C:32]2[S:33][C:34]([CH3:38])=[C:35]([CH3:37])[N:36]=2)[CH2:29][C:30]=1[O:31][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:22][CH2:23][CH3:24])[CH3:18]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 79634-MethylpyridineHCID 136010418HCID 136010418, compound

Product 1

HCID 54148715HCID 54148715, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.12 g) and 4-methylpyridine (0.08 g) were added dropwise with stirring to a solution of 2-[1-(ethoxyimino)butyl]-5-(4,5-dimethyl-2-thiazolyl)-3-hydroxycyclohex-2-en-1-one (2) (0.27 g) in dichloromethane (40 ml) at ambient temperature. After 1 hour the solution was washed with cold dilute aqueous sodium hydroxide, followed by cold dilute hydrochloric acid and then dried over magnesium sulphate and evaporated to give 2-[1-(ethoxyimino)butyl]-3-benzoyloxy-5-(4,5-dimethyl-2-thiazolyl)cyclohex-2-en-1-one (0.28 g, 80%) as an orange oil. The product was characterized by proton nuclear magnetic resonance spectroscopy and appropriate physical data are recorded in Example 5 Table 6.

Workup

  1. washAfter 1 hour the solution was washed with cold dilute aqueous sodium hydroxide
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-b48302bbe0ba47c5bbd758275bff5ac9
Source dataset
uspto-grants-1987_11
Patent number
US04704157

Reaction notes

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