Diisopropylethylamine → HCID 18672331、化合物

HRID 1058311ノート

反応式

HRID 1058311 の反応式
CCN(C(C)C)C(C)C.Cl.[OH:11][CH:12]1[CH2:15][NH:14][CH2:13]1.Br[CH2:17][C:18]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:19]=1[C:20]#[N:21]>C(Cl)Cl>[Cl:26][C:23]1[CH:24]=[CH:25][C:18]([CH2:17][N:14]2[CH2:15][CH:12]([OH:11])[CH2:13]2)=[C:19]([CH:22]=1)[C:20]#[N:21]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 126680522-(Bromomethyl)-5-chlorobenzonitrile

生成物 1

HCID 18672331HCID 18672331、化合物収率 82.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

DIEA (3.57 mL, 20.50 mmol) was added to a stirred mixture of 3-hydroxyazetidine hydrochloride (1.00 g, 9.11 mmol) and 2-bromomethyl-5-chlorobenzonitrile (2.10 g, 9.11 mmol) in CH2Cl2 (75 mL). After 16 h the reaction mixture was concentrated and the residue was partitioned between ether and 1N HCl. The aqueous layer was washed with ether, made neutral with NaHCO3, saturated with NaCl and extracted into CH2Cl2. The organic layer was dried (Na2SO4) and evaporated to give 5-chloro-2-[(3-hydroxyazetidin-1-yl)methyl]benzonitrile (1.67 g) as a gum: 1H NMR (CDCl3, 400 MHz) δ 3.03 (m, 2H), 3.68 (m, 2H), 4.49 (t, J=6.2 Hz, 1H), 7.46 (d, J=8.6 Hz, 1H), 7.53 (d,d, J=2.2, 6.2 Hz, 1H), 7.60 (d, J=2.0 Hz, 1H).

後処理

  1. concentrationAfter 16 h the reaction mixture was concentrated
  2. customthe residue was partitioned between ether and 1N HCl
  3. washThe aqueous layer was washed with ether
  4. extractionextracted into CH2Cl2
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-c6e3801d961f4c4a86bd28132ab8de7c
出典データセット
uspto-grants-2003_02
特許番号
US06515011B2

反応ノート

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