Hydrochloric Acid → HCID 67230167, compound

HRID 1038930Notes

Reaction equation

HRID 1038930 reaction equation
[OH-].[Na+].[I-].[CH3:4][S+](C)(C)=O.C[O:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:21][C:22]2[N:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:30](=[O:38])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)C=1O)=[O:13].Cl>CN(C=O)C.O>[OH:10][C:11]1[C:12]([O:13][CH3:4])=[CH:14][CH:19]=[CH:18][C:17]=1[C@H:16]1[CH2:20][C@H:21]1[C:22]1[N:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:30](=[O:38])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 136400710HCID 136400710, compound

Product 1

HCID 67230167HCID 67230167, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

NaOH (0.19 g, 4.8 mmol) was added to solution of trimethylsulfoxonium iodide (1.06 g, 4.8 mmol) in anhydrous DMF (20 mL) and stirred for 20 minutes. Then 69 (1 g, 2.4 mmol) was added in one portion and the reaction mixture was stirred for 2 hours at room temperature and left stirring overnight. The solution was poured into water, acidified by HCl to pH=6. The precipitate was filtered off and recrystallized from EtOH: H2O:DMF (1:1:1) mixture yielding 70 (0.14 g, 15%). M. Wt. 384. LCMS [M+H]+=385.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours at room temperature
  2. waitleft
  3. stirringstirring overnight
  4. filtrationThe precipitate was filtered off
  5. customrecrystallized from EtOH: H2O:DMF (1:1:1) mixture

Sources & evidence

ORD record
ord-3434983f288449d7bb54f4240b2920e6
Source dataset
uspto-grants-2013_10
Patent number
US08552009B2

Reaction notes

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