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

HRID 1003334Notes

Reaction equation

HRID 1003334 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][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.[CH3:20][N:21]=[C:22]=[O:23].CO.C(Cl)Cl>CCOC(C)=O.[Cu]Cl>[CH3:20][NH:21][C:22](=[O:23])[O:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:11][O:12][C:13]=2[CH:18]=1

Participants

6

Reactant 3

HCID 12228Methyl IsocyanateHCID 21226129Dichloromethane methanolHCID 1358150593-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol

Product 1

HCID 187964583-[[2-(4-Morpholinyl)ethyl]amino]1,2-benzisoxazol-6-yl methylcarbamateYield 28.8%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]amino]-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 h ours 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. Flash column chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM afforded a white solid which was recrystallized from EtOAc/pet. ether to yield 0.7 g of the expected product, m.p. 127-128° C.

Workup

  1. filtrationThe reaction was filtered through neutral alumina eluting with EtOAc (2 l)
  2. concentrationthe filtrate was concentrated in vacuo
  3. washFlash column chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM
  4. customafforded a white solid which
  5. customwas recrystallized from EtOAc/pet. ether

Sources & evidence

ORD record
ord-43adbcce41d34e75b188a5035ff4848c
Source dataset
uspto-grants-2000_04
Patent number
US06046203

Reaction notes

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