Isopropyl isocyanate → HCID 67764428, compound

HRID 1080687Notes

Reaction equation

HRID 1080687 reaction equation
[OH:1][CH2:2][C:3]1[C:7]([CH2:8][OH:9])=[C:6]([C:10]2C=CC=C[CH:11]=2)[N:5]([CH3:16])[C:4]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[CH3:23][CH:24]([N:26]=[C:27]=[O:28])[CH3:25]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.ClCCl>[CH3:23][CH:24]([NH:26][C:27](=[O:1])[OH:28])[CH3:25].[CH3:23][CH:24]([NH:26][C:27](=[O:1])[OH:28])[CH3:25].[N:20]1[CH:21]=[CH:22][C:17]([C:4]2[N:5]3[C:6](=[C:7]([CH2:8][OH:9])[C:3]=2[CH2:2][OH:1])[CH2:10][CH2:11][CH2:16]3)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 23365791HCID 23365791, compound

Product 1

HCID 67764428HCID 67764428, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 9798523Di-n-butyl diacetoxy tinCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the titled diol compound of Example VIII (1.6 g), 2-propylisocyanate (1.23 g) and dibutyltin diacetate (2 drops) in anhydrous dichloromethane (50 mL) was stirred at room temperature under an argon atmosphere for 15 hours. The mixture was concentrated in vacuo and the residue was subjected to flash chromatography to give the titled carbamate compound as an amorphous white powder (0.66 g) having a melting point of 160°-162° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-08f02d39089740d3af3fbfb899693864
Source dataset
uspto-grants-1996_12
Patent number
US05583148

Reaction notes

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