Thiourea → HCID 11637238, compound

HRID 1976121Notes

Reaction equation

HRID 1976121 reaction equation
Br[CH:2]1[CH2:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:4]=2[C:3]1=O.[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[F:13][C:11]1[CH:10]=[CH:9][C:5]2[CH2:6][CH2:7][CH2:8][C:2]3[S:17][C:16]([NH2:18])=[N:15][C:3]=3[C:4]=2[CH:12]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 22000390HCID 22000390, compound

Product 1

HCID 11637238HCID 11637238, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Bromo-3-fluoro-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one (1.0 g, 3.89 mmole) was mixed with thiourea (355 mg, 4.66 mmole) in 20 ml of ethanol and heated at reflux temperature for 16 hours. The reaction mixture was cooled and filtered to give a solid (m.p. 270° C.). The filtrate was concentrated and then partitioned between ethyl acetate and saturated sodium carbonate solution. The organic extract was concentrated and chromatographed (silica, ethyl acetate/hexanes) to give the desired product as a yellow solid (m.p. 142-144° C., 34%).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4b8656bd87fb4f6d9185071a43151fed
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

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