Water → HCID 18967775, compound

HRID 1450258Notes

Reaction equation

HRID 1450258 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:14]1([CH:17]([NH:25][CH2:26][CH2:27][CH3:28])[C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15]1.O>CC(C)=O>[C:5]([NH:3][C:2](=[S:1])[N:25]([CH:17]([CH:14]1[CH2:15][CH2:16]1)[C:18]1[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=1)[CH2:26][CH2:27][CH3:28])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 18967795HCID 18967795, compound2×

Product 1

HCID 18967775HCID 18967775, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

10.15 g of ammonium thiocyanate are suspended in 60 ml of acetone and the suspension is cooled to 0° C. 14.2 ml of benzoyl chloride dissolved in 15 ml of acetone are slowly added thereto. The mixture is left stirring for 15 minutes, followed by addition of 29 g of N-(α-cyclopropyl-4-bromobenzyl)-N-propylamine (Compound 32). The mixture is allowed to return to room temperature and stirring is continued for 2 hours. 20 ml of water are then added, followed by concentrating to the maximum extent. The residue is taken up in a mixture of water and methylene chloride. The organic phase is dried over anhydrous sodium sulphate and then concentrated and allowed to stand, to give the expected product in the form of yellow crystals.

Workup

  1. additionare slowly added
  2. waitThe mixture is left
  3. customto return to room temperature
  4. stirringstirring
  5. waitis continued for 2 hours
  6. concentrationby concentrating to the maximum extent
  7. additionThe residue is taken up in a mixture of water and methylene chloride
  8. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-459a4f77aed54fe6928170dfb5c790c7
Source dataset
uspto-grants-1997_02
Patent number
US05602132

Reaction notes

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