Hydrochloric Acid → HCID 22320514, compound

HRID 433165Notes

Reaction equation

HRID 433165 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:33][CH2:34][S:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([N:17](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:8]=2[N:32]=1)[CH2:2][CH2:3][CH3:4].Cl.[Cl:43]CCl>O1CCOCC1>[ClH:43].[CH2:1]([C:5]1[N:6]([CH2:33][CH2:34][S:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:32]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 22348368HCID 22348368, 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-13f30c030f5c4872b4c13ca7f18ddb38
Source dataset
uspto-grants-2003_12
Patent number
US06667312B2

Reaction notes

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