Isopropyl isocyanate → 3-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl 1-methylethylcarbamate

HRID 1292512ノート

反応式

HRID 1292512 の反応式
[N:1]1([CH2:7][CH2:8][N:9]([CH3:20])[C:10]2[C:14]3[CH:15]=[CH:16][C:17]([OH:19])=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:21][CH:22]([N:24]=[C:25]=[O:26])[CH3:23].CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:21][CH:22]([NH:24][C:25](=[O:26])[O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([N:9]([CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH3:20])=[N:11][O:12][C:13]=2[CH:18]=1)[CH3:23]

参加物

6

反応物 3

HCID 61277Isopropyl isocyanateHCID 21226129Dichloromethane methanolHCID 1358150583-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol

生成物 1

HCID 154351373-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl 1-methylethylcarbamate収率 41.7%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2.2 g) and copper(I)chloride (0.1 g) in EtOAc (50 ml) was added 1-methylethylisocyanate (0.8 g). After 24 hours TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (3 l) and the filtrate was concentrated in vacuo. The white solid was flash chromatographed on silica gel eluting with 1% MeOH/DCM to yield 1.2 g of the product, m.p. 99°-100° C.

後処理

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (3 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customchromatographed on silica gel eluting with 1% MeOH/DCM

出典と根拠

ORDレコード
ord-76d3bd80fa19407d88a27856aeb9030a
出典データセット
uspto-grants-1998_05
特許番号
US05756754

反応ノート

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