Benzyl isocyanate → N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(phenylmethyl)urea

HRID 1197687노트

반응식

HRID 1197687 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([NH:14][C:15]([NH:17]C3C=CC=CC=3)=[O:16])[C:7]=2[CH:24]=1)#[N:2].[CH2:25](N=C=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH2:9][CH:8]([NH:14][C:15]([NH:17][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:16])[C:7]=2[CH:24]=1)#[N:2]

참가 물질

4

반응물 2

HCID 76639Benzyl isocyanateHCID 9973362N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-phenylurea

생성물 1

HCID 15295557N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(phenylmethyl)urea수율 85.7%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of the title D compound from Example 8 (0.50 g, 2.47 mmoles) and benzyl isocyanate (0.33 g, 2.47 mmoles) in anhydrous ethanol (4 ml) was heated at reflux for 3 hours and cooled to room temperature. The reaction product precipitated from solution. It was collected by suction filtration; the solid was triturated with diisopropyl ether and dried under vacuum to obtain 0.71 g of the title compound as a white solid, m.p. 168-169° C. 1H NMR (DMSO-d6) δ 7.59 (s, 1 H), 7.56 (s, 1 H), 7.38-7.24 (m, 5 H) 6.89 (d, J=8.21 Hz, 1 H), 6.56 (t, J=5.87 Hz, 1 H), 6.50 (d, J=8.21 Hz, 1 H), 4.94 (M, 1 H), 4.30 (d, J=5.86 Hz, 2 H), 2.10 (m, 1 H), 1.74 (m, 1 H), 1.41 (s, 3 H), 1.28 (s, 3 H). 13C NMR (DMSO-d6) δ 158.11, 157.19, 140.78, 132.25, 132.08, 128.22, 126.93, 126.61, 126.12, 119.18, 118.03, 102.02, 77.28, 43.01, 41.95, 38.81, 29.08, 24.42.

후처리

  1. temperatureat reflux for 3 hours
  2. customThe reaction product precipitated from solution
  3. filtrationIt was collected by suction filtration
  4. customthe solid was triturated with diisopropyl ether
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-bc133ca288eb4053aaf03352a0267cdc
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05276168

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