Tetrahydrofuran → Cyclooctylthiourea

HRID 2360262Notes

Reaction equation

HRID 2360262 reaction equation
C([NH:9][C:10]([NH:12][CH:13]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].C1COCC1>CO.O>[CH:13]1([NH:12][C:10]([NH2:9])=[S:11])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 589299211-Benzoyl-3-cyclooctylthiourea

Product 1

HCID 14677887Cyclooctylthiourea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-benzoyl-3-cyclooctylthiourea (14.3 g, 49.1 mmol) and potassium carbonate (34.6 g, 250 mmol) in methanol (200 mL), water (100 mL), and THF (100 mL) was stirred at ambient temperature overnight. The low boiling solvents were removed in vacuo, and the residue was partitioned between EtOAc and water. The organic portion was washed with brine, and concentrated in vacuo. The title compound was obtained as a white solid after flash column chromatography (0 to 100% of ethyl acetate in hexanes). MS m/z: 187.1 (M+H)+.

Workup

  1. customThe low boiling solvents were removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic portion was washed with brine
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-497b3240b3ea4a94bf994b65959eba9b
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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