Formic Acid → HCID 68525343, compound

HRID 1990112Notes

Reaction equation

HRID 1990112 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]#[N:17])=[C:14]([S:18][CH3:19])[S:13][C:12]=2[C:20]([NH2:22])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C=O.C(O)=O>CC#N>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]#[N:17])=[C:14]([S:18][CH3:19])[S:13][C:12]=2[C:20]#[N:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 68524423HCID 68524423, compound

Product 1

HCID 68525343HCID 68525343, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add 3-(4-tert-butyl-phenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid amide(0.121 mmol) to 0.5 ml of CH3CN and add 18 mg paraformaldehyde and formic acid (1.59 mmol). Heat for 6 hrs. Concentrate and purify by radial chromatography eluting with ethyl acetate/hexanes to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 7.39 (q, 4H, J=12.0 Hz), 2.80 (s, 3H) and 1.42 (s, 9H).

Workup

  1. temperatureHeat for 6 hrs
  2. concentrationConcentrate
  3. custompurify by radial chromatography
  4. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-69c6207e7f0040cba999f725ea4a51d2
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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