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

HRID 1976124Notes

Reaction equation

HRID 1976124 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-f50796cb7f764038865d7fa733d0d4ca
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

Loading…