Hydrogen Sulfide → 4-(Benzyloxy)-3-propylbenzenecarbothioamide

HRID 603384Notes

Reaction equation

HRID 603384 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[CH2:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH2:20].C(NCC)C>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13](=[S:20])[NH2:14])=[CH:11][C:10]=1[CH2:17][CH2:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8021DiethylamineHCID 670187734-(Benzyloxy)-3-propylbenzonitrile

Product 1

HCID 593005514-(Benzyloxy)-3-propylbenzenecarbothioamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Through a solution of 4-(benzyloxy)-3-propylbenzonitrile (1.23 g, 4.91 mmol) (Example 30) in DMF (35 mL) was passed H2S for 30 min at rt. Diethyl amine (0.76 mL, 7.36 mmol) was added and the solution was heated to 60° C. for 4 h. The mixture was cooled to rt, and the residual H2S was removed by passing argon through the solution for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was filtered through a plug of silica and washed with EtOAc. Concentration of the filtrate under reduced pressure resulted in a yellow solid which was used in the next step without further purification.

Workup

  1. customfor 30 min
  2. customat rt
  3. temperatureThe mixture was cooled to rt
  4. customthe residual H2S was removed
  5. customfor 30 min
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. filtrationthe residue was filtered through a plug of silica
  8. washwashed with EtOAc
  9. customConcentration of the filtrate under reduced pressure resulted in a yellow solid which
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-03f2cd4aecd24bdb84df816f00c86983
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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