Thionyl Chloride → HCID 10268183, compound

HRID 991887Notes

Reaction equation

HRID 991887 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19]O)[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:23])=O>CCOCC>[ClH:23].[Cl:23][CH2:19][C:13]1[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 9856687HCID 9856687, compound

Product 1

HCID 10268183HCID 10268183, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Amino-1-(2-methylpropyl)-1H-imidazo-[4,5-c]quinoline-2-methanol (5.0 g; 0.0185 mol, Example 9) was added in small portions to vigorously stirred thionyl chloride (25 mL). The resulting mixture was stirred at room temperature overnight. The mixture was diluted with 100 mL of ether, and the solid was filtered from the mixture and dried thoroughly. The product was pure enough for further reactions. A sample was recrystallized from ethanol to give a pure product which melted with decomposition from 279-292° C. Analysis: Calculated: C, 55.4; H, 5.6; N, 17.2. Found: C, 55.3; H, 5.5; N, 17.1.

Workup

  1. filtrationthe solid was filtered from the mixture
  2. customdried thoroughly
  3. customA sample was recrystallized from ethanol
  4. customto give a pure product which
  5. custommelted with decomposition from 279-292° C

Sources & evidence

ORD record
ord-e2e0b5f6d067448e9bd65f186f59b4b5
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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