Diethyl Ether → HCID 22220851, compound

HRID 1836727Notes

Reaction equation

HRID 1836727 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
  3. temperatureheating
  4. waitwas continued 10 min
  5. customto separate
  6. customwhich crystalized
  7. waiton standing at room temp. overnight
  8. filtrationFiltration
  9. washwashing with 30% ether/acetonitrile
  10. customgave 1.86 g crude product which
  11. customevaporated to dryness
  12. customThe residue was recrystalized from acetonitrile/ether and from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-793524547ca847cdb7eac2902a0c7a04
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

Loading…