Ammonia → HCID 178474184, compound

HRID 1802619Notes

Reaction equation

HRID 1802619 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=S)=[CH:4][CH:3]=1.CI.N.CO.[CH2:20]([N:22](CC)CC)[CH3:21].C(Cl)(=[O:29])C>CC#N.CN(C=O)C.N1C=CC=CC=1.C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/2=[N:22]\[C:20](=[O:29])[CH3:21])=[CH:4][CH:3]=1

Participants

11

Reactant 6

HCID 222AmmoniaHCID 887MethanolHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86616333HCID 86616333, compound

Product 1

HCID 178474184HCID 178474184, compoundYield 28.9%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (384 mg, 1.23 mmol) in CH3CN (10 mL), CH3I (0.80 mL, 12.8 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo to give a solid. The solid was dissolved in DMF (6 mL). To the solution, NH3 in MeOH (7N, 3.0 mL, 21.0 mmol) and triethylamine (1.5 mL, 10.8 mmol) were added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give a solid. The solid was dissolved in pyridine (3 mL) and CH2Cl2 (3 mL). To the solution, acetyl chloride (0.200 mL, 2.8 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)acetamide (120 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a solid
  3. stirringAfter being stirred at room temperature overnight
  4. customthe mixture was purified by HPLC
  5. customto give a solid
  6. stirringAfter being stirred at room temperature overnight
  7. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-d0f72c3ea60b4fa3814944cec94806f9
Source dataset
uspto-grants-2013_01
Patent number
US08349873B2

Reaction notes

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