Methyl Isocyanate → 3-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl methylcarbamate

HRID 582861Notes

Reaction equation

HRID 582861 reaction equation
[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][N:22]=[C:23]=[O:24].CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:21][NH:22][C:23](=[O:24])[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

Participants

6

Reactant 3

HCID 12228Methyl IsocyanateHCID 21226129Dichloromethane methanolHCID 1358150583-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol

Product 1

HCID 154351353-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-yl methylcarbamateYield 49.8%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2 g) and copper(I)chloride (0.3 g) in EtOAc (60 ml) was added methyl isocyanate (0.5 g). After 3.5 hours thin layer chromatography (TLC) (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (2 l) and the filtrate was concentrated in vacuo to yield 1.2 g of the product, m.p. 94-95° C.

Workup

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (2 l)
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-46a377d3b01849ec91d06af538da711e
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Reaction notes

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