Ammonium thiocyanate → 3,4,4-Trifluoro-3-butenyl thiocyanate

HRID 132091

Reaction equation

Br[CH2:2][CH2:3][C:4]([F:8])=[C:5]([F:7])[F:6].[S-:9][C:10]#[N:11].[NH4+]>>[F:8][C:4](=[C:5]([F:7])[F:6])[CH2:3][CH2:2][S:9][C:10]#[N:11]

Participants

Reactant 2

HCID 15666Ammonium thiocyanate

HCID 663334-Bromo-1,1,2-trifluorobut-1-ene

Product 1

HCID 111479323,4,4-Trifluoro-3-butenyl thiocyanate

Procedure

When, for example, 4-bromo-1,1,2-trifluoro-1-butene and ammonium thiocyanate are used, 3,4,4-trifluoro-3-butenyl thiocyanate is obtained which is then reacted with H2S to give 3,4,4-trifluoro-3-butenyl dithiocarbamate. Further reaction of 3,4,4-trifluoro-3-butenyl dithiocarbamate with chloroacetaldehyde then provides 2-[(3,4,4-trifluoro-3-butenyl)sulphanyl]-1,3-thiazole. This reaction sequence may be schematically represented as follows:

Sources & evidence

ORD record: ord-08c9d0ac419944f8b680d33c62afbcb6
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07385093B2

Linked notes

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