Tetrahydrofuran → HCID 14579914, compound

HRID 2073508Notes

Reaction equation

HRID 2073508 reaction equation
O1C=CC([NH:6][CH2:7][C:8]#[N:9])=C1.C(N(CC)CC)C.[CH3:17][C:18]1[S:19][C:20]([C:24](Cl)=[O:25])=[C:21]([CH3:23])[N:22]=1.[O:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH3:17][C:18]1[S:19][C:20]([C:24]([NH:9][CH:8]([C:29]2[CH:30]=[CH:31][O:27][CH:28]=2)[C:7]#[N:6])=[O:25])=[C:21]([CH3:23])[N:22]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 146531402,4-Dimethylthiazole-5-carbonyl chlorideHCID 19891029HCID 19891029, compound

Product 1

HCID 14579914HCID 14579914, compound

Procedure

To a solution of 2-(3-furyl)aminoacetonitrile (1.46 g; 12 mmol) and triethylamine (1.20 g; 12 mmol) in tetrahydrofuran (30 ml) was added slowly a solution of 2,4-dimethylthiazole-5-carbonyl chloride (1.75 g; 10 mmol) in tetrahydrofuran (10 ml) with ice-cooling. After the addition, the mixture was turned to room temperature and stirring was continued for 3 hours. The solvent was removed under reduced pressure to separate the residue. Water was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude oil. The oil was purified by silica-gel column chromatography (eluent:n-hexane:ethyl acetate=2:1 by volume) to give 1.93 g of 2-(2,4-dimethylthiazole-5-carboxamido)-2-(3-furyl)acetonitrile as colorless crystals. m.p., 94°-96° C. Yield, 74%.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customwas turned to room temperature
  4. customThe solvent was removed under reduced pressure
  5. customto separate the residue
  6. additionWater was added to the residue, which
  7. extractionwas extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give crude oil
  12. customThe oil was purified by silica-gel column chromatography (eluent:n-hexane:ethyl acetate=2:1 by volume)

Sources & evidence

ORD record
ord-a8126a2ee68849008a48e222e73bb7c3
Source dataset
uspto-grants-1990_04
Patent number
US04918089

Reaction notes

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