Hydrochloric Acid → [2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol

HRID 1355437Notes

Reaction equation

HRID 1355437 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:5][CH:4]=1.Br[CH:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:15](OC)OC.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[C:20]1([C:14]2[S:11][C:10]([NH:9][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][OH:1])[N:8]=3)=[N:12][CH:15]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 11064658(1-Bromo-2,2-dimethoxyethyl)benzene2×HCID 18506916(6-Hydroxymethyl-pyridin-2-yl)-thiourea

Product 1

HCID 18506891[2-(5-Phenyl-thiazol-2-ylamino)-pyridin-6-yl]-methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(6-Hydroxymethyl-pyridin-2-yl)-thiourea (6-3) 1.05 g (5.73 mmol) and (1-bromo-2,2-dimethoxy-ethyl)-benzene (2.11 g, 8.60 mmol) were stirred in 18 mL EtOH. Concentrated HCl (aq), 6 mL, was added and the mixture was heated to reflux. After 7 h, additional (1-bromo-2,2-dimethoxy-ethyl)-benzene (1.05 g, 4.30 mmol) and conc HCl (aq), 3 mL were added. The reaction was then heated at reflux for an additional 14.5 h. The reaction was poured into 120 mL water and the pH was adjusted to 7 with Na2CO3 (s). A precipitate formed which was filtered and washed with water. The solid was triurated with 50 mL ether, filtered and washed with ether to provide the titled compound as a white solid. 1H NMR(CD3OD): δ7.72 (t, 1H, J=7.7 Hz), 7.58 (s overlapping with d, 3H), 7.38 (t, 2H, 7.5 Hz), 7.25 (t, 1H, J=7.3 Hz), 7.07 (d, 1H, J=7.5 Hz), 6.90 (d, 1H, J=8.3 Hz), 4.76 (s, 2H). Mp: 196-198° C. M+1: 284.0.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for an additional 14.5 h
  4. customA precipitate formed which
  5. filtrationwas filtered
  6. washwashed with water
  7. filtrationfiltered
  8. washwashed with ether

Sources & evidence

ORD record
ord-e8b962a8adb9427cb5038b94ba2a1810
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

Loading…