Methyl Isocyanate → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate

HRID 582869Notes

Reaction equation

HRID 582869 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:14]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:20][N:21]=[C:22]=[O:23].CC(C)=O.CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:20][NH:21][C:22](=[O:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][N:11]=[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[C:14]=2[CH:15]=1

Participants

6

Reactant 3

HCID 12228Methyl IsocyanateHCID 187964613-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-olHCID 21584259acetone MeOH DCM

Product 1

HCID 187964473-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamateYield 32.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135-136° C.

Workup

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (1 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was further purified by flash chromatography (silica gel)
  4. washeluting with 1:1:20 acetone/MeOH/DCM

Sources & evidence

ORD record
ord-3c25173fb72540b2bb1965aa31352bf1
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Reaction notes

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