1,2-Dichloroethane → 7-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

HRID 336472노트

반응식

HRID 336472 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)([O-:3])=[O:2].C(N(CC)CC)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[Cl:37][CH2:38][CH2:39][NH2:40].Cl>CN(C)C=O>[Cl:37][CH2:38][CH2:39][NH:40][C:13]([C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])=[O:15]

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 133692-ChloroethylamineHCID 757711-HydroxybenzotriazoleHCID 814097-nitro-1H-indole-2-carboxylic acid

생성물 1

HCID 866443587-Nitro-1H-indole-2-carboxylic acid (2-chloro-ethyl)-amide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

7-Nitro-1H-indole-2-carboxylic acid (371 mg, 3.2 mmol) prepared in Step A was dissolved in N,N-dimethylformamide (10 mL). Triethylamine (0.6 mL, 4.3 mmol), EDC (614 mg, 3.2 mmol) and HOBT (433 mg, 3.2 mmol) were added, 2-chloroethylamine (252.8 mg, 3.2 mmol) was added, and the mixture was stirred for 8 h at room temperature. 1N-hydrochloric acid solution was added, and the reaction mixture was extracted with ethyl acetate, washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled under reduced pressure to give the title compound.

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-cf5bcfdf3c694a3e80a1132a75036a36
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889691B2

반응 노트

불러오는 중…