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Hydrogen Sulfide → methyl (5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]-propoxy}-1H-indol-1-yl)acetate

HRID 2424962
Notes
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Reaction equation

HRID 2424962 reaction equation
[SH2:1].[CH3:2][O:3][C:4](=[O:31])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=3[CH2:28][CH2:29][CH3:30])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.C(NCC)C>CN(C=O)C>[CH3:2][O:3][C:4](=[O:31])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([NH2:27])=[S:1])=[CH:22][C:21]=3[CH2:28][CH2:29][CH3:30])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8021DiethylamineHCID 70971790methyl {5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate

Product 1

HCID 57845462methyl (5-{3-[4-(aminocarbonothioyl)-2-propylphenoxy]-propoxy}-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Hydrogen sulfide was passed through a solution of methyl{5-[3-(4-cyano-2-propylphenoxy)propoxy]-1H-indol-1-yl}acetate (Example 51, 787 mg, 1.94 mmol) in DMF (15 mL) for 30 minutes at rt. Diethyl amine (0.3 mL, 2.90 mmol) was added, and the solution was heated to 70° C. for 3 h. The reaction mixture was cooled to rt, and the residual H2S was removed by passing argon through the reaction mixture for 30 minutes. The solvent was evaporated under reduced pressure and the residue was filtered through a plug of silica and washed with EtOAc. Concentration of solvent yielded a brown oil which was used in the next step without further purification. LC/MS m/z 441.2 (M+H)+; RT 3.35 min.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe residual H2S was removed
  3. customfor 30 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. filtrationthe residue was filtered through a plug of silica
  6. washwashed with EtOAc
  7. customConcentration of solvent yielded a brown oil which
  8. customwas used in the next step without further purification
  9. customRT 3.35 min.

Sources & evidence

ORD record
ord-baae1535e12540f89a35e269c54f67a5
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07964622B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes