Thionyl Chloride → HCID 67052428, compound

HRID 599449Notes

Reaction equation

HRID 599449 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C:6]1[C:15]2[N:16]=[C:17]([CH2:23]O)[N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]=2[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=1>ClCCCl>[ClH:3].[Cl:3][CH2:23][C:17]1[N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:14]2[C:13]3[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=3[N:7]=[C:6]([NH2:5])[C:15]=2[N:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10149351HCID 10149351, compound

Product 1

HCID 67052428HCID 67052428, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Thionyl chloride (2.65 mL, 36.2 mmol) was added dropwise to a stirred suspension of [4-amino-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methanol (4.97 g, 18.1 mmol) in 1,2-dichloroethane (200 mL). The suspension dissolved, then a precipitate formed after 5 minutes. The reaction mixture was stirred at room temperature for 6 hours, then was concentrated under reduced pressure to yield crude 2-(chloromethyl)-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride, all of which was used in the next step.

Workup

  1. dissolutionThe suspension dissolved
  2. customa precipitate formed after 5 minutes
  3. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-94fa83fcaf204321ae733c5cba3e64d7
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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