4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 69219983, compound

HRID 272697

Reaction equation

HRID 272697 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18][CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:12][C:13]1[N:14]=[CH:15][S:16][C:17]=1[CH2:18][CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

6

Reactant 4

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 69219983HCID 69219983, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-amino-3-nitrophenol (386 mg, 2.5 mmol), 2-(4-methyl-1,3-thiazol-5-yl)ethanol (0.299 mL, 2.5 mmol), polymer supported triphenylphosphine (1.25 g, 3 mmol/g, 3.75 mmol), and di-tert-butyl azodicarboxylate (864 mg, 3.75 mmol) in THF (10 mL) was stirred at room temperature for 16 hours. Filtered through Celite and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide 602 mg (86%) of the desired product. MS (DCI) m/e 279 (M+H)+, 1H NMR (300 MHz, DMSO-d6): □ 8.83 (s, 1H), 7.37 (d, J=3.05 Hz, 1H), 7.25 (s, 2H), 7.16 (dd, J=8.99, 2.88 Hz, 1H), 7.01 (s, 1H), 4.10 (t, J=6.27 Hz, 2H), 3.19 (t, J=6.27 Hz, 2H), 2.35 (s, 3H).

Workup

  1. filtrationFiltered through Celite
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-409df72e33cf45d8a976a3b4eefceee5
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

Loading…