Water → 1-Benzoyl-3-(3-bromo-5-iodophenyl)-thiourea

HRID 1941920Notes

Reaction equation

HRID 1941920 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.[Br:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([I:22])[CH:21]=1)[NH2:18].O>CC(C)=O>[C:5]([NH:3][C:2]([NH:18][C:17]1[CH:19]=[C:20]([I:22])[CH:21]=[C:15]([Br:14])[CH:16]=1)=[S:1])(=[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 454803883-Bromo-5-iodoaniline

Product 1

HCID 578136521-Benzoyl-3-(3-bromo-5-iodophenyl)-thioureaYield 84.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of ammonium thiocyanate (4.45 g, 0.0585 mol) in anhydrous acetone (48 ml) was treated dropwise with benzoyl chloride (6.47 ml, 0.05583 mol) and stirred at ambient temperature for 1 h. A solution of 3-Bromo-5-iodoaniline (15.85 g, 0.05319 mol) in anhydrous acetone (48 ml) was then added in one portion and the mixture stirred at ambient temperature for 16 h. The resultant suspension was poured into water (300 ml) and stirred for 0.5 h. The precipitated solid was collected by filtration washed with water followed by 40-60° petroleum ether and dried in vacuo to afford 1-Benzoyl-3-(3-bromo-5-iodo-phenyl)-thiourea (20.70 g, 84%).

Workup

  1. stirringthe mixture stirred at ambient temperature for 16 h
  2. stirringstirred for 0.5 h
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customfollowed by 40-60°
  6. customdried in vacuo

Sources & evidence

ORD record
ord-38b458a17c4d4c9aa24067542cae88f5
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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