Cyanamide → HCID 178513446, compound

HRID 909376Notes

Reaction equation

HRID 909376 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[N:10][CH:11]=2)[CH2:2]1.[N:16]#[C:17][NH2:18].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CC#N>[F:14][C:12]([F:15])([F:13])[C:9]1[N:10]=[CH:11][C:6]([CH:3]2[CH2:4][CH2:5][S:1](=[N:18][C:17]#[N:16])[CH2:2]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 59265967HCID 59265967, compound

Product 1

HCID 178513446HCID 178513446, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(Tetrahydrothiophen-3-yl)-2-trifluoromethylpyridine (1.082 g, 4.64 mmol) was dissolved in 9 mL anhydrous CH3CN under nitrogen. The solution was cooled in an ice bath. Solid cyanamide (0.195 g, 4.64 mmol) was added followed by iodobenzene diacetate (1.496 g, 4.64 mmol). The reaction mixture was allowed to slowly warm to room temperature overnight. The solution was extracted with hexane (6×30 mL). The acetonitrile layer was concentrated by rotary evaporation, and the residue was triturated with ether. The resulting solid was collected and washed with ether to yield (1E)-3-[6-(trifluoromethyl)pyridin-3-yl]tetrahydro-1H-1λ4-thien-1-ylidenecyanamide (1.12 g; 88.4% yield) as an off-white powder. The 1H NMR spectrum of this solid exhibited resonances for a 1:1 mixture of diastereomers. 1H NMR (acetone-d6) δ 8.85 (d, J=2.2 Hz, 1H, pyridine H6), 8.83 (d, J=2.2 Hz, 1H, pyridine H6), 8.26 (dd, J=2.2, 8.3 Hz, 1H, pyridine H4), 8.15 (dd, J=2.2, 8.3 Hz, 1H, pyridine H4), 7.90 (d, J=8.3 Hz, 1H, pyridine H3), 7.86 (d, J=8.3 Hz, 1H, pyridine H3), 4.38 (dd, J=8.7, 14 Hz, 1H), 4.23 (tt, J=6, 12 Hz, 1H), 4.16 (ddd, J=2.6, 8.3, 11.2 Hz, 1H), 3.83 (td, J=8.7, 18 Hz, 1H), 3.68-3.48 (m, 3H), 3.29-3.17 (m, 2H), 2.95 (m, 1H), 2.85-2.79 (m, 3H), 2.33 (m, 1H). LC-MS (ELSD): 273 [m]+.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionThe solution was extracted with hexane (6×30 mL)
  3. concentrationThe acetonitrile layer was concentrated by rotary evaporation
  4. customthe residue was triturated with ether
  5. customThe resulting solid was collected
  6. washwashed with ether

Sources & evidence

ORD record
ord-10d4eec648ec48b4acd3659c3ef3a99e
Source dataset
uspto-grants-2011_09
Patent number
US08017788B2

Reaction notes

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