Benzoyl isothiocyanate → tert-butyl N-[(4-{[(benzoylamino)carbothioyl]amino}cyclo-hexyl)methyl]carbamate

HRID 917493Notes

Reaction equation

HRID 917493 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][CH2:3]1.[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[C:17]([NH:25][C:26]([NH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:4][CH2:3]1)=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 218825401,1-Dimethylethyl N-((4-aminocyclohexyl)methyl)carbamate

Product 1

HCID 15524265tert-butyl N-[(4-{[(benzoylamino)carbothioyl]amino}cyclo-hexyl)methyl]carbamateYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl N-[(4-aminocyclohexyl)methyl]carbamate (4.683 g, 20.5 mmol) and benzoyl isothiocyanate (3.77 g, 23.1 mmol) in 180 ml THF was stirred at room temperature for 20 hours. The solvent was removed in vacuo to yield a golden viscous oil. The oil was triturated with 250 ml hexane and the resulting solid was collected by filtration and washed with hexane. The off-white solid was washed several times with hexane and was dried under vacuum to yield 91% (7.32 g) of the desired product as an off-white solid: 1H-NMR (CDCl3) δ 1.20 (6H, m), 1.44 (9H, s), 1.83 (2H, m), 2.25 (2H, m), 3.01 (2H, t, J=6.4 Hz), 4.20 (1H, m), 4.62 (1H, m), 7.51 (2H, t, J=7.9 Hz), 7.60 (1H, t, J=7.4 Hz), 7.81 (2H, d, J=7.2 Hz), 8.93 (1H, s); 392 (ESMS, MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield a golden viscous oil
  3. customThe oil was triturated with 250 ml hexane
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with hexane
  6. washThe off-white solid was washed several times with hexane
  7. customwas dried under vacuum

Sources & evidence

ORD record
ord-6a5154e9f0c94fa89dfc40dc78edaea4
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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