1,2-Dichloroethane → 6-Methyl-2-(4-phenoxyanilino)-3,1-benzoxazin-4-one

HRID 430948

反応式

HRID 430948 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O:12]([C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=O)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)CCl>C1COCC1.CN(C=O)C>[CH3:11][C:8]1[CH:9]=[CH:10][C:2]2[N:1]=[C:26]([NH:25][C:22]3[CH:23]=[CH:24][C:19]([O:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:20][CH:21]=3)[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 762552-Amino-5-methylbenzoic acidHCID 27348964-Phenoxyphenyl isocyanate

生成物 1

HCID 187626196-Methyl-2-(4-phenoxyanilino)-3,1-benzoxazin-4-one収率 40.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-amino-5-methylbenzoic acid (172 mg, 1.10 mmol) in THF (1 ml) was treated with 4-phenoxyphenyl isocyanate (241 mg, 1.10 mmol). The mixture was kept at room temperature for 24 h, during which time the solvent was allowed to evaporate to leave a pale brown solid. This was dissolved in DMF (5 ml) and added to a suspension of PS-EDC (0.8 mmol g−1, 2.8 g) in DMF (20 ml). The resulting mixture was agitated at room temperature for 18 h, after which the resin was filtered off and washed with DMF (2×5 ml). The filtrate and washings were combined and evaporated under reduced pressure. Flash column chromatography over silica (20% ethyl acetate in hexane as eluent) afforded the required compound as an off-white solid (153 mg, 40%); δH (400 MHz, DMSO-d6) 2.36 (3H, s, CH3), 6.96 (2H, d, J8, Ph), 7.04 (1H, d, J8, Ph), 7.09 (1H, t, J8, Ph), 7.26 (1H, d, J8, Ph), 7.34-7.38 (2H, m, Ph), 7.55-7.56 (1H, m, Ph), 7.76-7.78 (4H, m, Ph); m/z (ES+) 345 (MH+).

後処理

  1. customto evaporate
  2. customto leave a pale brown solid
  3. filtrationafter which the resin was filtered off
  4. washwashed with DMF (2×5 ml)
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-968c7d63c3a24b6584b88a298f7d5129
出典データセット
uspto-grants-2003_12
特許番号
US06656934B2

関連ノート

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