Cyanamide → HCID 178513450, compound

HRID 1924849Notes

Reaction equation

HRID 1924849 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][S:10]C)=[CH:4][N:3]=1.[N:12]#[C:13][NH2:14].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C1COCC1>[F:8][C:7]1[CH:6]=[C:5]([CH2:9][SH:10]=[N:14][C:13]#[N:12])[CH:4]=[N:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 592970862-Chloro-3-fluoro-5-methylthiomethylpyridine

Product 1

HCID 178513450HCID 178513450, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-chloro-3-fluoro-5-methylthiomethylpyridine (1.7 g, 8.9 mmol) and cyanamide (3.7 g, 8.9 mmol) in THF (15 mL) cooled to 0° C. was added iodobenzene diacetate (2.86 g, 8.9 mmol) in one portion and the resulting mixture was stirred at 0° C. for 1 h and then at room temperature for 2 h. The solvent was removed in vacuo and the resulting mixture was purified on silica gel using 60% acetone in hexane to give 1.828 g of [1-(5-fluoro-6-chloropyridin-3-yl)methyl]-λ4-sulfanylidenecyanamide as an off-white solid in 89% yield. LC-MS calcd. for C8H7ClFN3S [M+1]+: 232.69. Found: 232.04.

Workup

  1. waitat room temperature for 2 h
  2. customThe solvent was removed in vacuo
  3. customthe resulting mixture was purified on silica gel using 60% acetone in hexane

Sources & evidence

ORD record
ord-74c8e622b3d94efaaabdfddd527b1833
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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