Water → 5-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide
Reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[Cl:8][C:9]1[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C.O>C1COCC1>[OH:4][CH2:3][C:2]([NH:1][S:14]([C:12]1[S:13][C:9]([Cl:8])=[C:10]([N+:18]([O-:20])=[O:19])[CH:11]=1)(=[O:16])=[O:15])([CH2:5][OH:6])[CH3:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-amino-2-methyl-1,3-propanediol (0.44 g, 4.2 mmol) in THF (10 ml) was added at room temperature 5-chloro-4-nitrothiophene-2-sulfonyl chloride (1.0 g, 3.82 mmol) and triethylamine (0.58 ml, 4.2 mmol). The light yellow suspension was stirred at room temperature for 17 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and subsequent crystallization from ethyl acetate/hexane to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-amide (0.25 g, 20%) as a light brown solid. Mp 133° C.
Workup
- extractionextracted with dichloromethane (3×75 ml)
- washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) and subsequent crystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-107c5dafc12e49d3b4b554a158e77119
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361659B2
Reaction notes
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