Bromopinacolone → HCID 53891096, compound

HRID 1179218Notes

Reaction equation

HRID 1179218 reaction equation
Br[CH2:2][C:3](=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[NH2:9][NH:10][C:11]([NH2:13])=[S:12]>C(O)C>[C:4]([C:3]1[N:13]=[C:11]([NH:10][NH2:9])[S:12][CH:2]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 21642BromopinacoloneHCID 2723789Thiosemicarbazide

Product 1

HCID 53891096HCID 53891096, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-bromo-3,3-dimethyl-butan-2-one (1.35 mL, 10 mmol) and thio-semicarbazide (0.91 g, 10 mmol) in ethanol (35 mL) was refluxed for 1.5 h and evaporated. Purification by flash chromatography (SiO2) provided (4-tert-butyl-thiazol-2-yl)-hydrazine (1.01 g, 59% yield) as an orange solid. 1H-NMR (DMSO-d6, 500 MHz) 9.0 (br, 1H), 7.3 (br, 2H), 6.37 (s, 1H), 1.22 (s, 9H) ppm; MS (LC-MS) 172.1 (M+H); HPLC (method A) 2.520 min.

Workup

  1. temperaturewas refluxed for 1.5 h
  2. customevaporated
  3. customPurification by flash chromatography (SiO2)

Sources & evidence

ORD record
ord-0a626895f8384da4b89c3a6e1c437b34
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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