Acetaldehyde → HCID 60207423, compound

HRID 1192203Notes

Reaction equation

HRID 1192203 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][NH:19][CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23].[CH:26](=O)[CH3:27].[Na]>O1CCCC1.C(O)(=O)C.C(OC(=O)C)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][N:19]([CH2:26][CH3:27])[CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23]

Participants

7

Reactant 3

HCID 177AcetaldehydeHCID 5360545SodiumHCID 60207421HCID 60207421, compound

Product 1

HCID 60207423HCID 60207423, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(pyrrolidin-3-yl)thiophene-2-carboxamide (0.1 g, 0.24 mmol) and acetaldehyde (31.9 mg, 0.72 mmol) in tetrahydrofuran (3.0 mL) under nitrogen, was added 2 drops of acetic acid. The resulting mixture was stirred at ambient temperature for 30 minutes. Then sodium triacetoxyboronhidride was added and the reaction mixture was stirred at ambient temperature for additional 12 hours. After this time, the reaction mixture was diluted with ethylacetate and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 90:10 mixture of dichloromethane and methanol as eluent to afford the title product as a solid (40 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 7.57 (1H, m), 7.44 (1H, m), 7.06 (1H, m), 4.07 (2H, m), 3.81 (3H, s), 3.812 (3H, s), 3.807 (2H, s), 2.33 (2H, m), 2.13 (6H, s), 1.86 (2H, m). MS m/z: 268.26 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for additional 12 hours
  2. washwashed with brine and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography
  7. additiona 90:10 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-a44dbe976b3e479b912fc0b7728e99d9
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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