Hydrochloric Acid → N-[(DIBUTYLAMINO)THIOXOMETHYL]-BENZAMIDE

HRID 1859375Notes

Reaction equation

HRID 1859375 reaction equation
[S-:1][C:2]#[N:3].[K+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:14]([NH:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17].Cl>CC(C)=O>[CH2:14]([N:18]([CH2:19][CH2:20][CH2:21][CH3:22])[C:2]([NH:3][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[S:1])[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 8148DibutylamineHCID 516872Potassium thiocyanate

Product 1

HCID 2762433N-[(DIBUTYLAMINO)THIOXOMETHYL]-BENZAMIDEYield 63.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 36.93 g (380 mmol) of potassium thiocyanate in 600 ml of acetone was added dropwise over 15 mins, 53.42 g (380 mmol) of benzoyl chloride. The resultant mixture was heated at reflux for 20 mins. To this mixture was added over 10 mins, 51.70 g (400 mmol) of dibutylamine. The mixture was stirred for 3 hrs and poured into a solution of 100 ml of concentrated HCl and 800 ml of ice. The yellow solid precipitate was collected, washed with water and recrystallized from isopropanol. The white solid was collected and dried to give 70.12 g of product (63.1% yield); mp: 90-93° C. The NMR spectrum was consistent with the proposed structure. Anal. Calcd. for C16H24N2OS: C, 65.7; H, 8.3; N, 9.6; S, 11.0. Found: C, 65.84; H, 8.25; N, 9.61; S, 10.7.

Workup

  1. temperatureat reflux for 20 mins
  2. additionTo this mixture was added over 10 mins
  3. customThe yellow solid precipitate was collected
  4. washwashed with water
  5. customrecrystallized from isopropanol
  6. customThe white solid was collected
  7. customdried

Sources & evidence

ORD record
ord-dd5d1f2b4b274558bf043efe0e957ec8
Source dataset
uspto-grants-2003_03
Patent number
US06528223B1

Reaction notes

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