Methyl Isocyanate → 4-(2-Hydroxybenzylideneamino)naphth-1-yl methylcarbamate

HRID 434721

반응식

HRID 434721 반응식
[OH:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH:4]=[N:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][CH:7]=1.[CH3:21][N:22]=[C:23]=[O:24]>C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.O1CCCC1>[CH3:21][NH:22][C:23](=[O:24])[O:16][C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([N:5]=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]=2[OH:1])=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 12228Methyl IsocyanateHCID 1356896084-(2-Hydroxybenzylideneamino)-1-naphthol

생성물 1

HCID 1356896174-(2-Hydroxybenzylideneamino)naphth-1-yl methylcarbamate수율 100%

시약·촉매·용매 2

HCID 9798523Di-n-butyl diacetoxy tin촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a 350 milliliter glass pressure bottle equipped with a magnetic stirrer was added 4.00 grams (0.015 moles) of 4-(2-hydroxybenzylideneamino)-1-naphthol prepared in Part A, 1.03 grams (0.018 moles) of methyl isocyanate, 100 milliliters of tetrahydrofuran and 5 drops of dibutyl tin diacetate. The resulting reaction mixture was stirred for 18 hours at room temperature after which the volatiles were removed under reduced pressure and the remaining residue dissolved in ether. The ethereal solution was washed twice with a 1% aqueous sodium bicarbonate solution and twice with a saturated brine solution, dried over magnesium sulfate and concentrated under reduced pressure to give 4.87 grams (0.015 moles) of 4-(2-hydroxybenzylideneamino)naphth-1-yl methylcarbamate in the form of a pale yellow solid having a melting point of 143°-145.5° C. and the following structural formula: ##STR16##

후처리

  1. customThe resulting reaction mixture
  2. customwere removed under reduced pressure
  3. dissolutionthe remaining residue dissolved in ether
  4. washThe ethereal solution was washed twice with a 1% aqueous sodium bicarbonate solution and twice with a saturated brine solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-877c77b0d6394bb6abe197c36150f87d
출처 데이터셋
uspto-grants-1983_08
특허 번호
US04399148

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