Benzoyl isothiocyanate → HCID 86731951, compound

HRID 1616700Notes

Reaction equation

HRID 1616700 reaction equation
[NH2:1][C:2]1[S:11][C:5]2[CH2:6][O:7][CH:8]([CH3:10])[CH2:9][C:4]=2[C:3]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[C:19]([NH:27][C:28](=[S:29])[NH:1][C:2]1[S:11][C:5]2[CH2:6][O:7][CH:8]([CH3:10])[CH2:9][C:4]=2[C:3]=1[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86731952HCID 86731952, compound

Product 1

HCID 86731951HCID 86731951, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-amino-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.104 g, 0.386 mmol, 1 eq) in dry ethanol (1 mL) under argon was added benzoyl isothiocyanate (0.15 mL, 1.08 mmol, 2.8 eq). The mixture was heated at reflux for 16 hours. The solvent was evaporated in vacuo. Purification by reverse-phase chromatography (10-100% CH3CN: Water ramp over 20 min) afforded the desired product tert-butyl 2-(3-benzoylthioureido)-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate as a pale yellow oil (0.057 g, 0.132 mmol, 34% yield). 1H NMR (400 MHz, DMSO) δ 14.72 (s, 1H), 11.89 (s, 1H), 8.06-7.95 (m, 2H), 7.69 (t, J=7.4, 1H), 7.57 (t, J=7.7, 2H), 4.78 (d, J=14.8, 1H), 4.66 (d, J=15.0, 1H), 3.80-3.63 (m, 1H), 2.93 (d, J=16.7, 1H), 2.50-2.44 (m, 1H), 1.59 (s, 9H), 1.30 (d, J=6.1, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was evaporated in vacuo
  4. customPurification by reverse-phase chromatography (10-100% CH3CN: Water ramp over 20 min)

Sources & evidence

ORD record
ord-37dbe6f006be48b3923e30be9d733bdb
Source dataset
uspto-grants-2014_07
Patent number
US08765803B1

Reaction notes

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