Thiourea → HCID 11637238, compound

HRID 917490Notes

Reaction equation

HRID 917490 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-c79725920ed84952952c56ea071f48ce
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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