Dimethylformamide → (6-Hydroxymethyl-pyridin-2-yl)-thiourea

HRID 1355436Notes

Reaction equation

HRID 1355436 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C([N:23]=[C:24]=[S:25])(=O)C1C=CC=CC=1>C(Cl)Cl>[OH:9][CH2:8][C:6]1[N:7]=[C:2]([NH:1][C:24]([NH2:23])=[S:25])[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68284Benzoyl isothiocyanateHCID 111826066-Amino-2-pyridinemethanol

Product 1

HCID 18506916(6-Hydroxymethyl-pyridin-2-yl)-thiourea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Amino-pyridin-2-yl)-methanol (6-2, 1.00 g, 8.06 mmol) was dissolved in 20 mL anhydrous CH2Cl2 and 5 mL anhydrous DMF under N2. Benzoylisothiocyanate (1.19 mL, 8.86 mmol) was added and the reaction was stirred at room temperature fro 16 h. The reaction was concentrated in vacuo and to the resulting residue was added 24 mL 1M NaOH (aq) and 24 mL TEF. The resulting mixture was heated to reflux for 3 h. The THF was removed in vacuo and a white precipitate formed. The mixture was filtered and washed with water to provide the titled compound as a white solid. 1H NMR(DMSO-d6): δ10.58 (bs, 1H), 10.48 (bs, 1H), 8.84 (bs, 1H), 7.74 (t, 1H, J=8.1 Hz), 7.06 (d, 1H, J=7.5 Hz), 7.01 (d, 1H, J=8.1 Hz), 5.47 (t, 1H, J=5.9 Hz), 4.47 (d, 2H, J=5.7 Hz).

Workup

  1. concentrationThe reaction was concentrated in vacuo and to the resulting residue
  2. additionwas added 24 mL 1M NaOH (aq) and 24 mL TEF
  3. temperatureThe resulting mixture was heated
  4. temperatureto reflux for 3 h
  5. customThe THF was removed in vacuo
  6. customa white precipitate formed
  7. filtrationThe mixture was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-b046cb1af0f04b2fb5be65704265217e
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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