Methyl Bromide → 1,1′-[(1Z,3Z)-2,3-Diisocyano-1,3-butadiene-1,4-diyl]bis[4-methoxybenzene]

HRID 1033764Notes

Reaction equation

HRID 1033764 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\[N+:22]#[C-:23])/[C:11](/[N+:20]#[C-:21])=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.[C:24](=O)([O-])[O-].[K+].[K+].CBr>CN(C=O)C>[CH3:24][O:19][C:16]1[CH:15]=[CH:14][C:13](/[CH:12]=[C:11](/[C:10](/[N+:22]#[C-:23])=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)\[N+:20]#[C-:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6323Methyl BromideHCID 11430Potassium CarbonateHCID 6441021xanthocillin X monomethyl ether

Product 1

HCID 64444531,1′-[(1Z,3Z)-2,3-Diisocyano-1,3-butadiene-1,4-diyl]bis[4-methoxybenzene]Yield 110.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13 mg of xanthocillin X monomethyl ether is dissolved in 2 ml of DMF and 40 mg of potassium carbonate is added thereto. Further, 50 μl of methyl bromide is added thereto and the mixture thus formed is extracted with 30 ml portions of ethyl acetate thrice. The extracts are combined, successively washed with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate. The sodium sulfate is filtered off, and the solvent is distilled from the filtrate. Thus, approximately 15 mg of xanthocillin X dimethylether is obtained in the form of a yellow solid.

Workup

  1. customthe mixture thus formed
  2. extractionis extracted with 30 ml portions of ethyl acetate thrice
  3. washsuccessively washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  5. filtrationThe sodium sulfate is filtered off
  6. distillationthe solvent is distilled from the filtrate

Sources & evidence

ORD record
ord-d829a9f6a9e3427fb3b337f5dbb314b0
Source dataset
uspto-grants-1994_05
Patent number
US05312833

Reaction notes

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