Hydrochloric Acid → HCID 178521144, compound

HRID 1042046Notes

Reaction equation

HRID 1042046 reaction equation
[I-].C([O:6][C:7](=O)[CH2:8][CH2:9][C:10]([O:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[O+:18]=[C:17]2[C:27]([C:30]3[CH:39]=[CH:38][C:33]4[O:34][CH2:35][CH2:36][O:37][C:32]=4[CH:31]=3)=[CH:28][S:29][C:16]=12)=[O:11])(C)(C)C.[ClH:41].S(Cl)([Cl:44])=O>ClCCl>[Cl-:44].[Cl:41][C:7](=[O:6])[CH2:8][CH2:9][C:10]([O:12][CH2:13][O:14][C:15]1[CH:20]=[C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[O+:18]=[C:17]2[C:27]([C:30]3[CH:39]=[CH:38][C:33]4[O:34][CH2:35][CH2:36][O:37][C:32]=4[CH:31]=3)=[CH:28][S:29][C:16]=12)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 178451072HCID 178451072, compound

Product 1

HCID 178521144HCID 178521144, compoundYield 134.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial was charged with a magnetic stirring bar, 7-((4-tert-butoxy-4-oxobutanoyloxy)methoxy)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-morpholinothieno[3,2-b]pyran-4-ium iodide (81) (1.02 g, 1.49 mmol), dichloromethane (4.7 mL) and hydrochloric acid (4 M in dioxane, 1.49 mL, 5.95 mmol). The solution was magnetically stirred at room temperature for 30 minutes. The reaction was charged with thionyl chloride (1.63 mL, 2.98 mmol) and stirred at room temperature overnight. The reaction solution was concentrated in mow to give 7-((4-chloro-4-oxobutanoyloxy)methoxy)-3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-morpholinothieno[3,2-b]pyran-4-ium chloride (82) (1.12 g, 2.01 mmol) as a crunchy yellow solid.

Workup

  1. additionA vial was charged with a magnetic stirring bar
  2. stirringstirred at room temperature overnight
  3. concentrationThe reaction solution was concentrated in mow

Sources & evidence

ORD record
ord-59dfe766223c415fb5776a7bad7b42ab
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Reaction notes

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