Hydrochloric Acid → HCID 56597620, compound

HRID 509094Notes

Reaction equation

HRID 509094 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:18]([N:21](CC2C=CC(OC)=CC=2OC)[C:22]2[S:26][N:25]=[CH:24][N:23]=2)(=[O:20])=[O:19])[CH:6]=[CH:7][C:8]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)#[N:2].Cl>O1CCOCC1>[C:1]([C:3]1[CH:4]=[C:5]([S:18]([NH:21][C:22]2[S:26][N:25]=[CH:24][N:23]=2)(=[O:19])=[O:20])[CH:6]=[CH:7][C:8]=1[S:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66652799HCID 66652799, compound

Product 1

HCID 56597620HCID 56597620, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 3-cyano-N-(2,4-dimethoxybenzyl)-4-[(3-methoxyphenyl)thio]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 17, 0.204 g, 0.368 mmol) was added a 4M solution of hydrogen chloride in 1,4-dioxane. The reaction was stirred at ambient temperature overnight. The reaction was quenched with methanol and passed through a plug of Arbocel™ to give a pale yellow solution. The solution was concentrated in vacuo to give a yellow solid. The solid was purified by silica gel flash column chromatography to give a white solid (0.141 g, 95%).

Workup

  1. customThe reaction was quenched with methanol
  2. customto give a pale yellow solution
  3. concentrationThe solution was concentrated in vacuo
  4. customto give a yellow solid
  5. customThe solid was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-f14fb3c054b44790bf825df6eaf2c685
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Reaction notes

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