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

HRID 252822노트

반응식

HRID 252822 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3cfb3bde3a114e6b8bd6c702bc945bd4
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868205B2

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