Hexane → N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamide

HRID 1436067Notes

Reaction equation

HRID 1436067 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:14][OH:15].CCCCCC>O1CCCC1>[CH2:16]([C:13]([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[S:11])([CH2:14][OH:15])[CH2:18][CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 8058HexaneHCID 68284Benzoyl isothiocyanateHCID 143256072-Amino-2-ethylbutan-1-ol

Product 1

HCID 86618579N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl isothiocyanate (4.28 mL, 31.8 mmol) was added under nitrogen to a solution of 2-amino-2-ethylbutan-1-ol (3.7315 g, 31.8 mmol), prepared in the previous step, in 100 mL of anhydrous tetrahydrofuran (exotherm on addition). After the addition, the reaction was refluxed for 2.5 h. After cooling to room temperature, 100 mL of hexane was added. The solid that formed was collected by filtration and dried under reduced pressure to give N-({[1-ethyl-1-(hydroxymethyl)propyl]amino}carbonothioyl)benzamide (7.1406 g, 80%) as a white solid, mp 161-163° C.; MS (ESI) m/z 281 [M+H]+.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction was refluxed for 2.5 h
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a8d2be81528f4cd6aee68e536b550742
Source dataset
uspto-grants-2009_11
Patent number
US07618989B2

Reaction notes

Loading…