tert-Butyl methyl ether → HCID 21078943, compound

HRID 1374932Notes

Reaction equation

HRID 1374932 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[OH:12])=[O:4].[CH3:13][C:14]1[N:15]=[CH:16][S:17][C:18]=1[CH3:19].COC(C)(C)C>C(#N)C>[Br-:1].[OH:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N+:15]1[C:14]([CH3:13])=[C:18]([CH3:19])[S:17][CH:16]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 625104,5-DimethylthiazoleHCID 1510171-(2,4-Dihydroxyphenyl)-2-bromoethanone

Product 1

HCID 21078943HCID 21078943, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

The neat mixture of 2-bromo-2′,4′-dihydroxyacetophenone (3 g, 13 mmol) and 4,5-dimethylthiazole (1.71 g, 13.3 mmol) was heated at 110° C. for 3 hrs. It was dissolved in acetonitrile (15 mL) and cooled to room temperature. Tert-butyl methyl ether (5 mL) was added and the reaction mixture kept at room temperature overnight. The product crystallized was filtered, washed well with a mixture of acetonitrile and tert-butyl methyl ether (1:1, v/v) and dried. It was recrystallized from a mixture of methanol and a few drops of water. Yield: 2.5 g (50%); mp. 257–260° C. (dec.).

Workup

  1. temperaturecooled to room temperature
  2. customThe product crystallized
  3. filtrationwas filtered
  4. washwashed well with a mixture of acetonitrile and tert-butyl methyl ether (1:1
  5. customv/v) and dried
  6. customIt was recrystallized from a mixture of methanol and a few drops of water

Sources & evidence

ORD record
ord-88413c5657dc4659b6675155681e1aab
Source dataset
uspto-grants-2007_01
Patent number
US07166625B2

Reaction notes

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