Diethyl Ether → HCID 22220851, compound

HRID 1794036Notes

Reaction equation

HRID 1794036 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([OH:8])[CH3:7].[Cl:9][CH2:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12].C(#N)C.CCOCC>CO>[Cl-:9].[OH:8][CH:6]([C:2]1[S:1][CH:5]=[CH:4][N+:3]=1[CH2:10][C:11](=[O:12])[N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH3:7]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342Acetonitrile2×HCID 884401-(Chloroacetyl)pyrrolidineHCID 99892952-Thiazolemethanol, alpha-methyl- (7CI,9CI)

Product 1

HCID 22220851HCID 22220851, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(2-Thiazolyl)ethanol (1.14 g, 8.8 mmole), N-chloroacetylpyrrolidine (1.30 g, 8.8 mmole), and acetonitrile (1.25 mL) were combined and heated at reflux in an oil bath at 105–110 C for 6 hr. Acetonitrile (8 mL) was added and heating was continued 10 min. The cooled, clear solution was treated with ether (10 mL), causing an oil to separate, which crystalized on standing at room temp. overnight. Filtration and washing with 30% ether/acetonitrile gave 1.86 g crude product which was dissolved in methanol, decolorized, and evaporated to dryness. The residue was recrystalized from acetonitrile/ether and from methanol/acetonitrile/ether to yield 1.63 g of the title compound, mp 189–190 C (dec.).

Workup

  1. temperatureheated
  2. temperatureat reflux in an oil bath at 105–110 C for 6 hr
  3. temperatureheating
  4. customto separate
  5. customwhich crystalized
  6. waiton standing at room temp. overnight
  7. filtrationFiltration
  8. washwashing with 30% ether/acetonitrile
  9. customgave 1.86 g crude product which
  10. customevaporated to dryness
  11. customThe residue was recrystalized from acetonitrile/ether and from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-39ba1c4ef4d3464e979d8a9240055043
Source dataset
uspto-grants-2006_04
Patent number
US07022721B1

Reaction notes

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