Sodium Hydroxide → 3-[[(4-Tert-butylphenyl)sulfonyl](methyl)amino]thiophene-2-carboxylic acid

HRID 1925706ノート

反応式

HRID 1925706 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([O:23]C)=[O:22])[CH3:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([OH:23])=[O:22])[CH3:15])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 59180428Methyl 3-(4-tert-butyl-n-methylphenylsulfonamido)thiophene-2-carboxylate

生成物 1

HCID 251833753-[[(4-Tert-butylphenyl)sulfonyl](methyl)amino]thiophene-2-carboxylic acid収率 436.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

In an appropriate microwave vessel, a solution of 56 (0.129 g; 0.35 mmol) in dioxane (2 mL) at 25° C. was added aqueous sodium hydroxide (1.5 mL; 3.0 mmol; 2M). The vessel was sealed and brought to 110° C. for 10 minutes via the Biotage Initiator Microwave Synthesizer. Upon cooling to 25° C., the mixture was diluted with water (10 mL) and washed with diethyl ether (5 mL). The aqueous layer was treated with concentrated hydrochloric acid to pH 1 and extracted with dichloromethane (2×20 mL). The organic layers were combined, washed with water (5×25 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title product (0.54 g).

後処理

  1. customThe vessel was sealed
  2. washwashed with diethyl ether (5 mL)
  3. additionThe aqueous layer was treated with concentrated hydrochloric acid to pH 1
  4. extractionextracted with dichloromethane (2×20 mL)
  5. washwashed with water (5×25 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-498cb5cc4dd44158b488cbddc0d1f5d1
出典データセット
uspto-grants-2012_05
特許番号
US08178699B2

反応ノート

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