Dimethylformamide → [5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea

HRID 1355441Notes

Reaction equation

HRID 1355441 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.CN(C=O)C.C([N:25]=[C:26]=[S:27])(=O)C1C=CC=CC=1>C(Cl)Cl.O>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:26]([NH2:25])=[S:27])=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 68284Benzoyl isothiocyanateHCID 185068066-amino-3-Pyridinepropanol

Product 1

HCID 18506785[5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-(6-Amino-pyridin-3-yl)-propan-1-ol (7-3), 2.83 g (19.5 mmol) was stirred in 15 mL of anhydrous CH2Cl2 under Ar. Anhydrous DMF, 5 mL was added and the solution became homogeneous. Benzoylisothiocyanate (2.62 mL, 19.5 mmol) was added and after 2 h the reaction was concentrated in vacuo. To the residue was added 60 mL 1 M NaOH, and 120 mL THF and the resulting mixture was heated to reflux. After 2 h reaction was cooled to RT, and diluted with water (pH 9). The aqueous phase was extracted three times with EtOAc. The combined organic phases was dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (gradient: CH2Cl2 to 95:5 CH2Cl2/MeOH) to afford the pure titled compound. 1H NMR (DMSO-d6) δ10.57 (bs, 1H), 10.43 (bs, 1H), 8.80 (bs, 1H), 8.05 (d, 1H, J=2.3 Hz), 7.62 (dd, 1H, J=2.4, 8.6 Hz), 7.10 (d, 1H, J=8.7 Hz), 4.48 (t, 1H, J=3.0 Hz), 3.41 (m, 2H), 2.59 (t, 2H, J=6.9 Hz), 1.68 (m, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. additionTo the residue was added 60 mL 1 M NaOH, and 120 mL THF
  3. temperaturethe resulting mixture was heated to reflux
  4. customAfter 2 h reaction
  5. extractionThe aqueous phase was extracted three times with EtOAc
  6. dry with materialThe combined organic phases was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography (gradient: CH2Cl2 to 95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-f973f31eb8c144a090ded37b2689bec9
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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