p-Toluenesulfonic acid → HCID 86608776, compound

HRID 1508396Notes

Reaction equation

HRID 1508396 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:11]([C:12](=[S:15])[NH:13][NH2:14])[N:10]=[C:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:8]1)=[N+:2]=[N-:3].[CH3:30]OC(OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:11]([C:12]2[S:15][CH:30]=[N:14][N:13]=2)[N:10]=[C:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 86608777HCID 86608777, compound

Product 1

HCID 86608776HCID 86608776, compoundYield 90%

Conditions

Temperature
80 °C

Procedure

2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbothiohydrazide (220 mg, 0.51 mmol) was dissolved in trimethyl-orthoformate (1.62 g, 15.2 mmol) with a few crystals of pTsOH (10 mg, 0.05 mmol), and heated to 80° C. for 20 minutes. The reaction mixture was then concentrated and purified by flash column chromatography, eluting with 4:1 (hexanes/ethyl acetate), to afford the desired product as a light yellow oil (202 mg, 90%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by flash column chromatography
  3. washeluting with 4:1 (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-1a81165357ae4c6bb02511ca1abd67fc
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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