Thiourea → 5-(t-Butyl)-2-oxazolylmethyl Thiouronium Hydrochloride

HRID 2182804Notes

Reaction equation

HRID 2182804 reaction equation
[C:1]([C:5]1[O:9][C:8]([CH2:10][Cl:11])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[ClH:11].[C:1]([C:5]1[O:9][C:8]([CH2:10][S:14][C:13]([NH2:15])=[NH2+:12])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 129689745-tert-Butyl-2-(chloromethyl)-1,3-oxazole

Product 1

HCID 224810765-(t-Butyl)-2-oxazolylmethyl Thiouronium HydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound of Example 6 (1.77 g, 10.2 mmol, 1.02 eq) was combined with thiourea (0.76 g, 9.98 mmol, 1 eq) under N2 in 10 mL of absolute ethanol. The reaction was heated at reflux for 1.5 hours. The mixture was cooled to room temperature and concentrated in vacuo. Trituration of the resulting crude material with t-butyl methyl ether provided 2.32 g (93%) of the title compound. HPLC R.T.=2.05 min (Phenomenex Inc., 5 μm C18 column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm); 1H NMR (d6-DMSO): δ 9.48 (s, 3H), 6.85 (s, 1H), 4.73 (s, 2H), 1.24 (s, 9H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cea2b3a76ad54c00a865638ff466262f
Source dataset
uspto-grants-2005_05
Patent number
US06897321B2

Reaction notes

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