Cyanamide → [1-(5-Fluoro-6-chloropyridin-3-yl)methyl](methyl)-lambda4-sulfanylidenecyanamide

HRID 2234217Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][S:10][CH3:11])=[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][S:10]([CH3:11])=[N:14][C:13]#[N:12])[CH:4]=[N:3][C:2]=1[Cl:1]

Participants

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](methyl)-λ4-sulfanylidenecyanamide as an off-white solid in 89% yield. LC-MS calcd. for C8H7ClFN3S [M+1]+: 232.69. Found: 232.04.

Workup

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

Sources & evidence

ORD record: ord-b106e8d793f34f788404eec0b3634ae4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709649B2

Reaction notes

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