Thiourea → HCID 58442473, compound

HRID 1465666Notes

Reaction equation

HRID 1465666 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16](=O)[CH2:17]Br)=[C:11]([CH3:20])[CH:10]=2)=[CH:4][CH:3]=1.[NH2:21][C:22]([NH2:24])=[S:23]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([C:16]3[N:21]=[C:22]([NH2:24])[S:23][CH:17]=3)=[C:11]([CH3:20])[CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 58442421HCID 58442421, compound

Product 1

HCID 58442473HCID 58442473, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(4-(4-bromophenylamino)-2,6-dimethylphenyl)-2-bromoethanone (1.6 g, 4.0 mmol) and thiourea (0.79 g, 7.2 mmol) in acetonitrile (30 mL) was heated at reflux for 90 min. The solution was concentrated and added with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL), and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give product (1.1 g), which was used directly for the next step without further purification.

Workup

  1. temperatureat reflux for 90 min
  2. concentrationThe solution was concentrated
  3. additionadded with water (50 mL) and saturated aqueous Na2CO3 (1.0 mL)
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous MgSO4(s)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbfcff4232a1494e98a54317463f33c8
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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