Toluene → HCID 19708127, compound
Reaction equation
[C:1]([N:5]=[C:6]=[S:7])([CH3:4])([CH3:3])C.C1([NH2:11])CC1.[C:12]1(C)C=C[CH:15]=[CH:14][CH:13]=1>>[CH:1]1([N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]([NH2:11])=[S:7])[CH2:3][CH2:4]1Participants
4
Procedure
t-Butyl isothiocyanate (11.6 ml, 0.1 mol) and cyclopropylamine (6.9 ml, 0.1 mol) were mixed in toluene (200 ml) and stirred at room temperature overnight. The resulting mixture was evaporated to a residue and crystallized from cyclohexane to yield N-cyclopropyl-N-butyl thiourea. N-cyclopropyl-N-t-butyl thiourea (5 g) was suspended in 5M HCl (50 ml) and heated to 80° C. for 10 minutes. The resulting solution was cooled, poured into a saturated sodium bicarbonate (250 ml), and extracted with ethyl acetate (2×125 ml). The solution was dried (MgSO4), evaporated to a residue and crystallized from ethyl acetate to yield a white solid, cyclopropyl thiourea, 110 mg.
Workup
- customThe resulting mixture was evaporated to a residue
- customcrystallized from cyclohexane
Sources & evidence
- ORD record
- ord-8cce94fe3e604f909f8a608ee5be4103
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05710324
Reaction notes
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