Sodium Cyanide → HCID 58597276, compound

HRID 1444705Notes

Reaction equation

Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[C-:17]#[N:18].[Na+]>CN1C(=O)CCC1>[C:17]([C:2]1[CH:16]=[CH:15][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1)#[N:18]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of N-(4-bromophenethyl)-2,2,2-trifluoroacetamide (2.96 g, 10 mmol), NiBr2 (2.19 g, 10 mmol) and NaCN (0.98 g, 20 mmol) in 2.0 mL of NMP was heated at 200° C. in microwave twice. After cooling down to RT, the mixture was filtered with the help excess of DCM. The filtrate was evaporated to dryness and was submitted to flash chomatography (SiO2, DCM to DCM/EtOAc=3:1) to give (N-(4-cyanophenethyl)-2,2,2-trifluoroacetamide was a white solid, together with 1.1 g for recovered starting material.

Workup

temperatureAfter cooling down to RT
filtrationthe mixture was filtered with the help excess of DCM
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-70163f39347c4e17ae67ac9bdd2fea76
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662811B2

Reaction notes

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