Phosphorus oxychloride → 5-[1-(Trifluoromethyl)cyclobutyl]-1,3,4-thiadiazol-2-amine

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1([C:7](O)=O)[CH2:6][CH2:5][CH2:4]1.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].P(Cl)(Cl)(Cl)=O>>[F:1][C:2]([F:11])([F:10])[C:3]1([C:7]2[S:15][C:14]([NH2:16])=[N:13][N:12]=2)[CH2:6][CH2:5][CH2:4]1

Participants

Reactant 3

HCID 24813Phosphorus oxychloride

HCID 2723789Thiosemicarbazide

HCID 27828381-(Trifluoromethyl)cyclobutanecarboxylic acid

Product 1

HCID 675457935-[1-(Trifluoromethyl)cyclobutyl]-1,3,4-thiadiazol-2-amine

Procedure

Commercially available, 1-(trifluoromethyl)cyclobutanecarboxylic acid (Oakwood), thiosemicarbazide (Aldrich) and phosphorus oxychloride (Aldrich) were processed as described for Example 1A to obtain the title compound. MS (ESI+) m/z 224 (M+H)+.

Sources & evidence

ORD record: ord-7d491b2187d14304abb08b0e2a1e130d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492371B2

Reaction notes

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