Triethylamine → 4-Amino-3-chloro-N,N-dimethylbenzamide

HRID 529648

반응식

HRID 529648 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].Cl.[CH3:13][N:14](C)[CH2:15]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CNC>C(Cl)Cl.C(O)(C)C.C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([CH3:15])[CH3:13])=[O:7])=[CH:4][C:3]=1[Cl:11]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 172114-Amino-3-chlorobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 202874814-Amino-3-chloro-N,N-dimethylbenzamide수율 59.6%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-amino-3-chloro-benzoic acid (1 equiv) in DCM (0.12 M) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.2 equiv), 1-hydroxybenzotriazole (1.2 equiv), triethylamine (4 equiv) and dimethylamine hydrochloride (2 equiv) sequentially. The mixture was stirred at room temperature overnight. After the reaction was complete, as monitored by LCMS, the mixture was diluted with a mixture of isopropanol in chloroform (30%,), washed with water and dried over anhydrous sodium sulfate. The organic phase was concentrated and the residue obtained was recrystallized in the mixture of hexane and ethyl acetate (10%,) to afford the desired product (Yield: 59.6%) as a light brown solid. MS (ESI) m/z 199.1 [M+1]+.

후처리

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe organic phase was concentrated
  4. customthe residue obtained
  5. customwas recrystallized in the mixture of hexane and ethyl acetate (10%,)

출처 및 근거

ORD 기록
ord-0187656467444a3f8b52cea66baa6d74
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346812B2

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