Thiourea → HCID 58442473, compound

HRID 1480724Notes

Reaction equation

HRID 1480724 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-99b546d2479b4c4fbfc6b582c75edcbd
Source dataset
uspto-grants-2016_08
Patent number
US09409902B2

Reaction notes

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