1-Isocyanato-4-methoxybenzene → HCID 19967417, compound

HRID 976619Notes

Reaction equation

HRID 976619 reaction equation
[CH:1]1([NH:9][OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[O:21])=[CH:15][CH:14]=1>O1CCCC1>[CH:1]1([N:9]([OH:10])[C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[O:21])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 18433785HCID 18433785, compound2×

Product 1

HCID 19967417HCID 19967417, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution containing cyclooctyl hydroxylamine (Compound 36 Part B, 2.0 g, 14 mmol) in tetrahydrofuran (50 mL) was slowly charged with 4-methoxyphenyl isocyanate (2.0 mL, 15 mmol). The reaction mixture was allowed to stir at ambient temperature for 20 hours. A white precipitate was isolated by filtration then washed with cold hexane. A second crop was isolated from the filtrate. The solids were combined and dried to provide 3.2 g of the desired product as a white solid, m.p. 166°-167° C. Analysis: Calculated for C16H24N2O3 : %C, 65.73; %H, 8.27; %N, 9.58; Found: %C, 65.31; %H, 7.98; %N, 9.47.

Workup

  1. customA white precipitate was isolated by filtration
  2. washthen washed with cold hexane
  3. customA second crop was isolated from the filtrate
  4. customdried

Sources & evidence

ORD record
ord-20e9ffd33c454921bbaaf1613ab86340
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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