Methyl Isocyanate → HCID 14302862, compound

HRID 2232121Notes

Reaction equation

HRID 2232121 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([OH:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[OH:16].[CH3:17][N:18]=[C:19]=[O:20]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([O:16][C:19](=[O:20])[NH:18][CH3:17])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]=1[O:15][C:19](=[O:20])[NH:18][CH3:17]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 14302861HCID 14302861, compound

Product 1

HCID 14302862HCID 14302862, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.00 g of 2,3-dimethoxy-1,4-dihydroxynaphthalene, prepared as shown in Preparation 5, in 50 ml of tetrahydrofuran was added 0.670 g of methyl isocyanate followed by 0.12 g of 4-dimethylaminopyridine. The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate, washed with dilute hydrochloric acid and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue chromatographed on silica gel, eluting with methylene chloride, giving 2,3-dimethoxy-1,4-di(methylcarbamoyloxy)naphthalene, m.p. 228°-229° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with dilute hydrochloric acid
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue chromatographed on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-8bc2160865294b04a325e651b84b5fa5
Source dataset
uspto-grants-1988_11
Patent number
US04786652

Reaction notes

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