Chlorosulfonyl isocyanate → Benzyl 4-(carbamoyloxy)-2-methylbenzoate

HRID 906082노트

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HRID 906082 반응식
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1.ClS([N:23]=[C:24]=[O:25])(=O)=O>ClCCl>[NH2:23][C:24]([O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[C:4]([CH3:18])[CH:3]=1)=[O:25]

참가 물질

4

반응물 2

HCID 70918Chlorosulfonyl isocyanateHCID 18006238Benzyl 4-hydroxy-2-methylbenzoate

생성물 1

HCID 67404605Benzyl 4-(carbamoyloxy)-2-methylbenzoate수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

To a solution of phenylmethyl 4-hydroxy-2-methylbenzoate (687 mg, 2.82 mmol) in dichloromethane (8 ml) at 0° C., was added chlorosulfonyl isocyanate (1.20 g, 8.50 mmol). The reaction was allowed to warm to 25° C. and stirred for 20 h. The reaction mixture was concentrated then taken into ethyl acetate and washed with water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford phenylmethyl 4-[(aminocarbonyl)oxy]-2-methylbenzoate (356 mg, 89%). 1H NMR (400 MHz, DMSO): 7.91-7.87 (d, 1H), 7.49-7.29 (m, 5H), 7.11-7.00 (m, 4H), 5.31 (s, 2H), 2.52 (s, 3H). MS (EI) for C16H15NO4: 286 (MH+).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-d334400bb4f94650bcbf2ca51b49736a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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