Thiourea → HCID 67279256, compound

HRID 1693144Notes

Reaction equation

HRID 1693144 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[Cl:5][CH2:6][C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19]>C(O)C>[ClH:5].[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]=1[CH2:6][S:3][C:2](=[NH:4])[NH2:1]

Participants

4

Reactant 2

HCID 2723790Thiourea2×HCID 57827368HCID 57827368, compound

Product 1

HCID 67279256HCID 67279256, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Thiourea (2.09 g) was added to a solution of 1-(2-chloromethylcyclohex-1-enyl)-2-fluorobenzene obtained in Preparation Example 1-(4) (5.88 g) in ethanol (200 mL). The reaction solution was heated to 80° C. and stirred for 270 minutes. Thiourea (399 mg) was added to the reaction solution, followed by stirring at the same temperature for one hour. After cooling to room temperature, the solvent was evaporated under reduced pressure. Diethyl ether and ethyl acetate were added to the residual syrup. A white solid was precipitated by ultrasonic treatment. After standing at room temperature for 30 minutes, the supernatant was removed. Further, the solid was washed with diethyl ether and the supernatant was removed again. The resulting solid was dried under reduced pressure to obtain the title compound (6.38 g).

Workup

  1. stirringby stirring at the same temperature for one hour
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionDiethyl ether and ethyl acetate were added to the residual syrup
  5. customA white solid was precipitated by ultrasonic treatment
  6. waitAfter standing at room temperature for 30 minutes
  7. customthe supernatant was removed
  8. washFurther, the solid was washed with diethyl ether
  9. customthe supernatant was removed again
  10. customThe resulting solid was dried under reduced pressure

Sources & evidence

ORD record
ord-88f24f019a0447148485de1440308abb
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

Loading…