Water → 5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonyl chloride

HRID 9428

Reaction equation

HRID 9428 reaction equation
[ClH:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]C(=N)N)[C:14]([CH2:25][O:26][CH2:27][CH3:28])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1.Cl([O-])(=O)=[O:30].[Na+].[OH2:34]>Cl>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]([Cl:1])(=[O:30])=[O:34])[C:14]([CH2:25][O:26][CH2:27][CH3:28])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516902Sodium ChlorateHCID 219844052-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride

Product 1

HCID 219842495-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride (1.49 g, 3.16 mmol) in 7 M hydrochloric acid (8 mL) was cooled to 0° C. A solution of sodium chlorate (0.44 g, 4.1 mmol) in water (1.0 mL) was added dropwise with stirring, and the reaction was stirred at 0° C. for one hour. A precipitate formed and was isolated by filtration, washed with ice-cold water (4×4 mL), and dried under high vacuum to provide 0.92 g of 5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentane-1-sulfonyl chloride as a yellow solid.

Workup

  1. stirringthe reaction was stirred at 0° C. for one hour
  2. customA precipitate formed
  3. customwas isolated by filtration
  4. washwashed with ice-cold water (4×4 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-f632421fc58442f9bc72226e808ac80b
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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