Methyl Isocyanate → 2'-[[(Methylamino)carbonyl]amino]methyl-3-bromo-1,1'-biphenyl-4-methanol

HRID 1379874ノート

反応式

HRID 1379874 の反応式
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1.[CH3:18][N:19]=[C:20]=[O:21]>C(Cl)Cl.CN(C)C=O.C(OCC)(=O)C>[CH3:18][NH:19][C:20]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([Br:17])[CH:10]=1)=[O:21]

参加物

6

反応物 2

HCID 12228Methyl IsocyanateHCID 218366552'-Aminomethyl-3-bromo-1,1'-biphenyl-4-methanol

生成物 1

HCID 218368052'-[[(Methylamino)carbonyl]amino]methyl-3-bromo-1,1'-biphenyl-4-methanol収率 88.4%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 68 mg (0.23 mmol) of 2'-aminomethyl-3-bromo-1,1'-biphenyl-4-methanol (Step H) in 3 mL of dry methylene chloride and 1 mL of dry dimethylformamide under nitrogen atmosphere at 0° C. was added 0.015 mL (0.25 mmol) of methyl isocyanate. The reaction mixture was stirred for 30 minutes at 0° C. then diluted with 100 mL of ethyl acetate, washed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give 71 mg (88%) of the product as a white solid which was used in the next step without further purification. 1H NMR (200 MHz, CD3 OD): δ 2.64 (s, 3H), 4.20 (s, 2H), 4.69 (s, 2H), 7.16 (m, 1H), 7.22-7.43 (m, 4H), 7.50 (d, 2 Hz, 1H), 7.58 (d, 8 Hz, 1H). FAB-MS: calculated for C16H17BrN2O2 349; found 349, 351 (80%).

後処理

  1. washwashed with water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-823ad1a921854a2581bff7cb21a9d85c
出典データセット
uspto-grants-1997_09
特許番号
US05672596

反応ノート

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