Triethylamine → HCID 67218909, compound

HRID 900877Notes

Reaction equation

HRID 900877 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:13]([C:11]1[S:12][C:8]([CH3:7])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=1)(=[O:15])=[O:14])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 214989645-Methyl-4-nitrothiophene-2-sulfonyl chloride

Product 1

HCID 67218909HCID 67218909, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-2-methyl-1-propanol (1.11 g, 12.4 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) 5-methyl-4-nitrothiophene-2-sulfonyl chloride [CAS No. 61714-77-0] and triethylamine (0.63 ml, 4.56 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate/MeOH) and subsequent crystallization (ethyl acetate/heptane) to yield 5-methyl-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.71 g, 58%) as a light brown solid. MS (ISP) 293.0 [(M−H)−]; mp 126° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate/MeOH) and subsequent crystallization (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-d26a6fd1b0a944549c9fbe71762a2cb2
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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