Ammonia → HCID 57813573, compound

HRID 1010640Notes

Reaction equation

HRID 1010640 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([I:8])[CH:7]=1.BrBr.N>C(Cl)(Cl)Cl.O>[I:1][C:2]1[CH:7]=[C:6]([I:8])[C:5]2[S:11][C:10]([NH2:12])=[N:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 57813558HCID 57813558, compound

Product 1

HCID 57813573HCID 57813573, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (3,5-diiodo-phenyl)-thiourea (4.0 g, 0.01 mol) in CHCl3 (160 mL) at −55-60° C. was added dropwise a solution of Br2 (4.72 g, 0.02 mol, in 25 ml of CHCl3) over a period of 15 min. The reaction mixture was stirred at −55-60° C. for 15 min followed by refluxing at 70-75° C. for 3 h. The reaction mixture was cooled to room temperature and filtered to get the crude residue that was washed with hexane and diethyl ether. The solid thus obtained was dissolved in H2O, basified with aqueous ammonia solution to pH 10-12 and stirred for 30 min. The solid thus obtained was filtered and washed with water to get the desired product (3.50 g, 88%).

Workup

  1. temperatureby refluxing at 70-75° C. for 3 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto get the crude residue that
  5. washwas washed with hexane and diethyl ether
  6. customThe solid thus obtained
  7. stirringstirred for 30 min
  8. customThe solid thus obtained
  9. filtrationwas filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-dd4c359c940c40f28f72140a11af09d0
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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