Triethylamine → Naphthalen-2-yl sulfamate

HRID 1494019노트

반응식

HRID 1494019 반응식
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[OH:18].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C.O>[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[O:18][S:2](=[O:3])(=[O:4])[NH2:5]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 86632-NaphtholHCID 70918Chlorosulfonyl isocyanate

생성물 1

HCID 21149346Naphthalen-2-yl sulfamate수율 107.5%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6342Acetonitrile용매3회HCID 8857Ethyl Acetate용매

실험 절차

To a cold (ice-acetone bath) solution of 11.3 ml (0.13 mole, 18.4 g) of chlorosulfonyl isocyanate in 50 ml of acetonitrile was added dropwise a solution of 2.3 g (0.13 mole) of water in 10 ml of acetonitrile at such a rate that the temperature was maintained between -2° to 7° C. (ca. 45 min). After the addition was complete, the solution was stirred for 5 min and then treated dropwise with a solution of 14.4 g (0.1 mole) of β-naphthol, 20.9 ml (0.15 mole, 15.2 g) of triethylamine and 100 ml of acetonitrile at such a rate that the temperature did not exceed 10° C. (ca. 30 min). The mixture was stirred at ambient temperature for 3.5 h and then diluted with 100 ml of ethyl acetate and 50 ml of water. The layers were separated and the organic layer was washed once with 50 ml of water and once with 100 ml of brine, dried (sodium sulfate), and concentrated to give 24 g of dark gum. The gum was purified by column chromatography on 400 g of silica gel eluted with methylene chloride. Fractions containing the desired product were combined and concentrated to yield 5.7 g (26%) of the title compound as a white solid, mp 114°-115° C. (benzene).

후처리

  1. temperaturewas maintained between -2° to 7° C. (ca. 45 min)
  2. additionAfter the addition
  3. customdid not exceed 10° C.
  4. custom(ca. 30 min)
  5. stirringThe mixture was stirred at ambient temperature for 3.5 h
  6. customThe layers were separated
  7. washthe organic layer was washed once with 50 ml of water and once with 100 ml of brine
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6a89d2acf2fc4336840c7f87621b5e2b
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05025031

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