Chloroacetone → HCID 86634762, compound

HRID 911078Notes

Reaction equation

HRID 911078 reaction equation
[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)=[CH:4][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[N:6][CH:7]=1.Cl[CH2:24][C:25](=O)[CH3:26].C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[C:3]([O:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][CH:17]=[N:18]3)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:24]=[C:25]([CH3:26])[N:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 86634787HCID 86634787, compound

Product 1

HCID 86634762HCID 86634762, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(5-bromo-4-(quinolin-5-yloxy)pyridin-2-yl)thiourea (2.00 g, 5.330 mmol), 1-chloropropan-2-one (0.6366 ml, 7.995 mmol), triethylamine (1.486 ml, 10.66 mmol), and ethanol (25 ml) was heated at reflux for two days. The organic solvents were concentrated, and hexanes:ethyl acetate (9:1) were added and the reaction was filtered. The residue was washed with water and ethyl acetate, and dried over high vacuum overnight to give the desired compound (1.70 g, 76.40% yield) as very light yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for two days
  3. concentrationThe organic solvents were concentrated
  4. additionhexanes:ethyl acetate (9:1) were added
  5. filtrationthe reaction was filtered
  6. washThe residue was washed with water and ethyl acetate
  7. customdried over high vacuum overnight

Sources & evidence

ORD record
ord-547562a543e3451f879d4474a4efd148
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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