Water → 4-(2-(2-Methoxyethoxy)ethylthio)-3-nitrobenzenesulfonamide

HRID 1045204Notes

Reaction equation

HRID 1045204 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][SH:10].F[C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23].O>O1CCCC1.C(OCC)(=O)C>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][S:10][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 114008022-(2-Methoxyethoxy)ethane-1-thiolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 671264604-(2-(2-Methoxyethoxy)ethylthio)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a 100 mL round-bottomed flask was added sodium hydride (0.6 g) in tetrahydrofuran (10 ml) to give a suspension. 2-(2-Methoxyethoxy)ethanethiol (1 g) was added slowly. After the mixture stirred for 30 minutes, 4-fluoro-3-nitrobenzenesulfonamide (1.616 g) in 10 ml tetrahydrofuran was added slowly. After the mixture stirred overnight, water was added slowly, and ethyl acetate (20 ml×3) was used to extract the product. The combined organic layers were dried over Na2SO4. After the mixture was filtered and concentrated, the crude product was added to a silica gel column and purified eluting with 0-10% methanol in dichloromethane.

Workup

  1. customto give a suspension
  2. stirringAfter the mixture stirred overnight
  3. extractionto extract the product
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationAfter the mixture was filtered
  6. concentrationconcentrated
  7. additionthe crude product was added to a silica gel column
  8. custompurified
  9. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-40a24b0ed0ef4ed2929a61448c03765b
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

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