Ethanol → HCID 178527812, compound

HRID 1838845Notes

Reaction equation

HRID 1838845 reaction equation
CC(C)CN[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[NH2:15].[C:17](=[S:19])=[S:18].C(O)C>[OH-].[Na+]>[S:18]1[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[C:17]1[SH:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 6348Carbon DisulfideHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 178527812HCID 178527812, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N4-(2-methylpropyl)quinoline-3,4-diamine (5.4 g, 25 mmol) was combined with carbon disulfide (9 mL, 150 mmol) and ethanol (55 mL) and then heated at reflux on a steam bath for 2 hours. The resulting precipitate was isolated by filtration, washed with ethanol and then air dried to provide 4.4 g of crude product. A portion (1 g) was dissolved in hot dilute sodium hydroxide and then reprecipitated with acetic acid. The precipitate was isolated by filtration while still hot, washed with hexane and then air dried to provide thiazolo[4,5-c]quinoline-2-thiol as a solid, m.p. 282-284° C. Analysis: Calculated for C10H6N2S2: %C, 55.02; %H, 2.77; %N, 12.83: Found: %C, 54.96; %H, 2.69; %N, 12.74.

Workup

  1. temperatureheated
  2. temperatureat reflux on a steam bath for 2 hours
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed with ethanol
  5. customair dried
  6. customto provide 4.4 g of crude product
  7. customreprecipitated with acetic acid
  8. customThe precipitate was isolated by filtration while still hot,
  9. washwashed with hexane
  10. customair dried

Sources & evidence

ORD record
ord-c5e570047b174d6b9dd5d7947551c60e
Source dataset
uspto-grants-2004_01
Patent number
US06677334B2

Reaction notes

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