Ethanol → HCID 68505578, compound

HRID 1508410Notes

Reaction equation

HRID 1508410 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)([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.CCO.[F:32][C:33]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:34]=1[C:35](=[S:38])[NH:36][NH2:37]>C(Cl)Cl>[Si:1]([O:18][CH2:19][CH2:20][C:21]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:37][N:36]=[C:35]([C:34]2[CH:39]=[C:40]([F:43])[CH:41]=[CH:42][C:33]=2[F:32])[S:38]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 54215325HCID 54215325, compoundHCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazide

Product 1

HCID 68505578HCID 68505578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tert-butyldiphenylsilyloxy)-1-phenylpropan-1-one (1.98 g, 5.10 mmol) in 20 mL of a 3:1 mixture of EtOH:DCM was added 2,5-difluorobenzothiohydrazide (0.800 g, 4.25 mmol). The mixture was allowed to stir capped, at room temperature for 60 hours, then uncapped for 48 hours and then concentrated in vacuo. The residue was purified by flash column chromatography (Hexanes) to afford the desired product as an orange oil, 2.19 g, 92% which was contaminated with 3-(tert-butyldiphenylsilyloxy)-1-phenylpropan-1-one. The compound was carried forward to the next step without further purification.

Workup

  1. customcapped, at room temperature for 60 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography (Hexanes)

Sources & evidence

ORD record
ord-669f17b86e1e4418b30eb8b51e311e74
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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