Benzoyl isothiocyanate → HCID 86608782, compound

HRID 1508411Notes

Reaction equation

HRID 1508411 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:25][N:24]=[C:23]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[S:22]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40]([N:48]=[C:49]=[S:50])(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1>[Si:1]([O:18][CH2:19][CH2:20][C:21]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:25]([C:49]([NH:48][C:40](=[O:47])[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[S:50])[N:24]=[C:23]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[S:22]1)([C:14]([CH3:15])([CH3:17])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 68505578HCID 68505578, compound

Product 1

HCID 86608782HCID 86608782, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (1.00 g, 1.79 mmol) in 20 mL of anhydrous THF was added benzoyl isothiocyanate (0.29 mL, 2.15 mmol). The reaction was allowed to stir overnight at reflux then cooled and concentrated in vacuo. The residue was purified by flash column chromatography (5-10% ethyl acetate/hexanes) to afford the desired product as a yellow foam, 0.677 g, 52%.

Workup

  1. temperatureat reflux
  2. temperaturethen cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography (5-10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-169700001ffa4e4a9405800c036cb8a9
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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