Chloroform → 1-(3-bromophenyl)thiourea

HRID 984712Notes

Reaction equation

HRID 984712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S-:9][C:10]#[N:11].[NH4+].S([O-])(O)=O.[Na+].C(Cl)(Cl)Cl>Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]([NH2:11])=[S:9])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 115623-BromoanilineHCID 15666Ammonium thiocyanateHCID 23665763Sodium Bisulfite

Product 1

HCID 27356191-(3-bromophenyl)thiourea

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-bromoaniline (10.89 ml, TCI) in 20% aqueous hydrochloric acid (18.2 ml) was added with ammonium thiocyanate (8.02 g, WAKO) and sodium hydrogensulfite (701 mg, WAKO) and stirred at 100° C. for 22 hours. The reaction mixture was added with chloroform (20 ml) for extraction. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 62, 4.45 g).

Workup

  1. customThe organic layer was dried
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-63191410607e48499eac385bb696a938
Source dataset
uspto-grants-2005_03
Patent number
US06867320B2

Reaction notes

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