Hydrochloric Acid → HCID 22320514, compound

HRID 897180Notes

Reaction equation

HRID 897180 reaction equation
C([C:5]1(C(C)(C)C)[C:14]2[N:13]=[C:12]([N:15](C([O-])=O)C([O-])=O)[C:11]3[N:22]=[C:23]([CH2:34][CH2:35][CH2:36][CH3:37])[N:24]([CH2:25][CH2:26][S:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:10]=3[C:9]=2[CH2:8][CH2:7][CH2:6]1)(C)(C)C.Cl.[Cl:43]CCl>O1CCOCC1>[ClH:43].[CH2:34]([C:23]1[N:24]([CH2:25][CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:14]=3[N:13]=[C:12]([NH2:15])[C:11]=2[N:22]=1)[CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 86759787HCID 86759787, compound

Product 1

HCID 22320514HCID 22320514, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, di(tert-butyl)2-butyl-1-[2-(phenylthio)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-ylimidodicarbonate (0.50 g, 0.86 mmol), a 4 M solution of hydrochloric acid in dioxane (5 mL), and dichloromethane (5 mL). The reaction was judged to be complete after stirring at ambient temperature for 2 hours. The volatiles were removed under reduced pressure to afford an off white solid. The material was recrystallized from acetonitrile to provide 2-butyl-1-[2-(phenylthio)ethyl]-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride (0.17 g, 1.30 mmol) as fluffy white needles, m.p. 237-238° C. Analysis. Calculated for C22H28N4S.(H2O)1/4.(HCl)2: % C, 57.70; % H, 6.71; % N, 12.23. Found C, 57.62; % H, 6.57; % N, 12.41.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customThe volatiles were removed under reduced pressure
  3. customto afford an off white solid
  4. customThe material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-1b5ca29304cb45bcb7f8a9b4862bcba8
Source dataset
uspto-grants-2005_07
Patent number
US06921826B2

Reaction notes

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