Water → HCID 11782405, compound

HRID 1096487Notes

Reaction equation

HRID 1096487 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([CH:19]=O)[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].O.[N+:27]([CH3:30])([O-:29])=[O:28]>>[N+:27](/[CH:30]=[CH:19]/[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][N:10]2[S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:9])=[O:8])([O-:29])=[O:28]

Participants

5

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 10107997HCID 10107997, compound

Product 1

HCID 11782405HCID 11782405, compound

Procedure

1-(Phenylsulfonyl)-1H-indole-4-carbaldehyde, Intermediate 5 (45.4 g, 0.159 mol) was dissolved in nitromethane (300 ml) and ammonium acetate (4.9 g, 0.064 mol, 0.4 eq.) was added. Mixture was heated at reflux for 4 hours and left overnight at ROOM TEMPERATURE Water (150 ml) was added, organic phase was separated. The aqueous phase was extracted with DCM (3×50 ml). Combined organic phase was washed with brine and dried on Na2SO4. The crude material (HPLC purity 85%) was passed through a silica column using DCM/EtOAc (8:1) as eluent. The product containing fractions were evaporated to a small volume when crystallization started. The yellow crystals were filtered, washed with petro/ether/EtOAc (2:1), and dried in vacuo. Yield: 33.1 g. MS m/z 329 [M+H]+.

Workup

  1. temperatureMixture was heated
  2. temperatureat reflux for 4 hours
  3. additionwas added
  4. customorganic phase was separated
  5. extractionThe aqueous phase was extracted with DCM (3×50 ml)
  6. washCombined organic phase was washed with brine
  7. customdried on Na2SO4
  8. additionThe product containing fractions
  9. customwere evaporated to a small volume when crystallization
  10. filtrationThe yellow crystals were filtered
  11. washwashed with petro/ether/EtOAc (2:1)
  12. customdried in vacuo

Sources & evidence

ORD record
ord-c1df5c869ba24d8b96d0b0c709ab7dce
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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