Trimethylorthoacetate → HCID 11959952, compound

HRID 2387616Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[S:13][C:12]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([C:21](=[S:24])[NH:22][NH2:23])[N:10]=1.[CH3:25][C:26](C)(C)C([O-])([O-])[O-]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[S:13][C:12]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([C:21]2[S:24][C:25]([CH3:26])=[N:23][N:22]=2)[N:10]=1

Participants

Reactant 2

HCID 21927715Trimethylorthoacetate

HCID 86608774HCID 86608774, compound

Product 1

HCID 11959952HCID 11959952, compoundYield 70.4%

Conditions

Temperature: 80 °C

Procedure

5-(2,5-difluorophenyl)-2-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carbothiohydrazide (0.268 g, 0.735 mmol) was weighed into a 25 mL 1 neck flask, and suspended in 9.0 mL of trimethylorthoacetate (0.088 g, 0.74 mmol). P-toluenesulfonic acid hydrate (0.0028 g, 0.015 mmol) was then added, and the reaction heated to 80° C. for 1 hour. The reaction was then concentrated in vacuo, and then purified by flash column chromatography (20-50% ethyl acetate/hexanes) yielding 0.201 g, 70% of the desired product as a white solid. MS ESI (+) m/z 389 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.56 (m, 2H), 7.34 (m, 2H), 7.27 (m, 2H), 7.08 (m, 2H), 2.59 (s, 3H), 2.56 (s, 3H).

Workup

concentrationThe reaction was then concentrated in vacuo
custompurified by flash column chromatography (20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-b71acaff129a457195fde4923cf568bf
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268871B2

Reaction notes

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