Water → (S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride

HRID 1523676ノート

反応式

HRID 1523676 の反応式
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([CH:7]=[N:8][OH:9])[CH2:4][O:3]1.[Cl:11]N1C(=O)CCC1=O.CCOCC.O>CN(C=O)C>[OH:9][N:8]=[C:7]([Cl:11])[C@@H:5]1[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]1

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 31398ChlorosuccinimideHCID 86644159(R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime

生成物 1

HCID 86644160(S)-N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride収率 78.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (R)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde oxime (10.3 g, 71.0 mmol) in 40 mL DMF was added 1-chloropyrrolidine-2,5-dione (10.4 g, 78.1 mmol) and the reaction was stirred overnight at ambient temperature. The reaction mixture was poured into ether (1400 mL) and water (500 mL). The ether layer was extracted with water (5×500 mL), dried over MgSO4, filtered and concentrated to (S)—N-hydroxy-2,2-dimethyl-1,3-dioxolane-4-carbimidoyl chloride (10.0 g, 55.7 mmol, 78.5% yield) as white solid.

後処理

  1. extractionThe ether layer was extracted with water (5×500 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-f9fcf7b7f4b64c358e58f835b679e715
出典データセット
uspto-grants-2015_07
特許番号
US09079890B2

反応ノート

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