1,2-Dichloroethane → N-(2-amino-5-carbamoylphenyl)-4-methoxybenzamide

HRID 252822ノート

反応式

HRID 252822 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1.[NH4+].[Cl-].C(Cl)CCl.CC[N:30](CC)CC>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[NH2:30])=[CH:4][C:3]=1[NH:11][C:12](=[O:21])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 597368674-Amino-3-(4-methoxybenzamido)benzoic acid

生成物 1

HCID 59736879N-(2-amino-5-carbamoylphenyl)-4-methoxybenzamide収率 30%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 108 (200 mg, 0.70 mmol), NH4Cl (74 mg, 1.40 mmol), HOBT-hydrate (104 mg, 0.77 mmol), EDC (119 mg, 0.77 mmol) and Et3N (0.29 ml, 2.1 mmol) in DMF (3 ml) was stirred for 16 h at room temperature. The solvent was evaporated, ethyl acetate was added and the organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl, dried over MgSO4, filtered and concentrated. The crude product was triturated in ethyl acetate and filtered to give the title compound 109 (60 mg, 30%). 1H NMR: (DMSO) δ (ppm): 9.57 (s, 1H), 7.96 (d, J=8.8 Hz, 2H), 7.67 (d, J=2.2 Hz, 1H), 7.59 (sb, 1H), 7.52 (dd, J=8.2, 2.0 Hz, 1H), 7.02 (d, J=8.8 Hz, 2H), 6.90 (sb, 1H), 6.72 (d, J=8.4 Hz, 1H), 5.41 (s, 2H), 3.83 (s, 3H). MS: (calc.) 285.1; (obt.) 286.1 (MH)+.

後処理

  1. customThe solvent was evaporated
  2. additionethyl acetate was added
  3. washthe organic layer was washed successively with saturated solutions of NH4Cl, NaHCO3 and NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was triturated in ethyl acetate
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-3cfb3bde3a114e6b8bd6c702bc945bd4
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

反応ノート

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