Chloroform → 1-(3-bromophenyl)thiourea

HRID 2378558Notes

Reaction equation

HRID 2378558 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, and the organic layer was dried. 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 74, 4.45 g).

Workup

  1. customthe organic layer was dried
  2. customThen, the 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-f027d3d982724b83aeca94ae33f97f83
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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