Benzyl isocyanate → [2-(4-Morpholinyl)ethylmethylamino]-1,2-benzisoxazol-6-yl phenylmethylcarbamate

HRID 582862Notes

Reaction equation

HRID 582862 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.N12CCCN=C1CCCCC2.[C:32]1([CH2:38][N:39]=[C:40]=[O:41])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[N-]=C=O>CCOC(C)=O.CO.C(Cl)Cl>[C:32]1([CH2:38][NH:39][C:40](=[O:41])[O:19][C:17]2[CH:16]=[CH:15][C:14]3[C:10]([N:9]([CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH3:20])=[N:11][O:12][C:13]=3[CH:18]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 76639Benzyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 105034IsocyanateHCID 1358150583-[[2-(4-Morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol

Product 1

HCID 15435136[2-(4-Morpholinyl)ethylmethylamino]-1,2-benzisoxazol-6-yl phenylmethylcarbamateYield 70.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]methylamino]-1,2-benzisoxazol-6-ol (2.3 g) and 1,8 diazabicyclo[5.4.0]undec-7-ene (0.2 g) in EtOAc (80 ml) was added phenylmethyl isocyanate (1.3 g). After 24 hours an additional equivalent of the isocyanate was added. TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was concentrated in vacuo. Flash chromatography (silica gel) eluting with 1% MeOH/DCM provided the product (2.4 g), m.p. 106-107° C.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washFlash chromatography (silica gel) eluting with 1% MeOH/DCM

Sources & evidence

ORD record
ord-8aea18798d794bec82e1336daaad0f14
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Reaction notes

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