Benzoyl isothiocyanate → HCID 86608782, compound

HRID 2040385Notes

Reaction equation

HRID 2040385 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-4b08e350db03438da337db50970f5460
Source dataset
uspto-grants-2013_11
Patent number
US08580828B2

Reaction notes

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