Acetonitrile → Cyclooctylthiourea

HRID 1199365Notes

Reaction equation

HRID 1199365 reaction equation
[CH:1]1([N:9]=[C:10]=[S:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCOC(C)=O.CCCCCC.CC#[N:26]>>[CH:1]1([NH:9][C:10]([NH2:26])=[S:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 2758001isothiocyanatocyclooctaneHCID 21226206Ethyl acetate hexane

Product 1

HCID 14677887CyclooctylthioureaYield 78.2%

Procedure

To a stirred solution of cyclooctyl isothiocyanate (7.26 g, 42.9 mmol) in 70 ml of CH3CN was added 8.5 ml of 15N NH4OH (130 mmol). The reaction progress was monitored by thin layer chromatography (TLC); 1/1 EtOAc/hexane. After 3 days, the reaction solution was concentrated, dissolved in 50 ml of ethyl acetate and washed with water (25 ml) and brine (aqueous saturated NaCl) (3×25 ml ea.). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica gel, 3/7 EtOAc/hexane) to yield 6.25 g (78.2%) of the desired thiourea. PMR(CDCl3)ppm 6.5 (bs, 1H), 6.00 (s, 2H), 4.35 (bs, 1/2H), 3.45 (bs, 1/2H), 2.1-1.3 (m, 14H). The melting point (MP) was 93°-95° C.

Workup

  1. concentrationthe reaction solution was concentrated
  2. dissolutiondissolved in 50 ml of ethyl acetate
  3. washwashed with water (25 ml) and brine (aqueous saturated NaCl) (3×25 ml ea.)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica gel, 3/7 EtOAc/hexane)

Sources & evidence

ORD record
ord-bb2edc2d130f4e5fa9fba7940aaae7ac
Source dataset
uspto-grants-1990_02
Patent number
US04900740

Reaction notes

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