Amidosulfenyl chloride, N,N-dibutyl- → N-(N,N-di-n-butylaminosulfenyl)-N-[4-(4-methylthiophenoxy)benzyl]4-chloro-1,3-dimethylpyrazole-5-carboxamide

HRID 257856

반응식

HRID 257856 반응식
[CH3:1][C:2]1[CH:26]=[CH:25][C:5]([S:6][C:7]2[CH:24]=[CH:23][C:10]([CH2:11][NH:12][C:13]([C:15]3[N:19]([CH3:20])[N:18]=[C:17]([CH3:21])[C:16]=3[Cl:22])=[O:14])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:27]([N:31]([CH2:34][CH2:35][CH2:36][CH3:37])[S:32]Cl)[CH2:28][CH2:29][CH3:30]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:27]([N:31]([CH2:34][CH2:35][CH2:36][CH3:37])[S:32][N:12]([CH2:11][C:10]1[CH:9]=[CH:8][C:7]([S:6][C:5]2[CH:25]=[CH:26][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:24][CH:23]=1)[C:13]([C:15]1[N:19]([CH3:20])[N:18]=[C:17]([CH3:21])[C:16]=1[Cl:22])=[O:14])[CH2:28][CH2:29][CH3:30]

참가 물질

5

반응물 2

HCID 81031Amidosulfenyl chloride, N,N-dibutyl-HCID 131717883N-[4-(4-methylthiophenoxy)benzyl]-4-chloro-1,3-dimethylpyrazole-5-carboxamide

생성물 1

HCID 131717882N-(N,N-di-n-butylaminosulfenyl)-N-[4-(4-methylthiophenoxy)benzyl]4-chloro-1,3-dimethylpyrazole-5-carboxamide수율 52%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

To a stirred mixture of N-[4-(4-methylthiophenoxy)benzyl]-4-chloro-1,3-dimethylpyrazole-5-carboxamide (300 mg, 0.746 mM), 4-(N,N-dimethylamino)pyridine (119 mg, 0.970 mM) and dry pyridine (5 ml) was added dropwise N,N-di-n-butylaminosulfenyl chloride (190 mg, 0.970 mM) at 0°-10° C., and the mixture was stirred for 4 h at the room temperature. The mixture was poured into ice water, and the mixture was extracted with dichloromethane. The extract was washed with saturated ammonium chloride solution(x2) and brine, dried with sodium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-(N,N-di-n-butylaminosulfenyl)-N-[4-(4-methylthiophenoxy)benzyl]4-chloro-1,3-dimethylpyrazole-5-carboxamide (217 mg, 52%) as a colorless oil, nD23.3 1.5748.

후처리

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated ammonium chloride solution(x2) and brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed over silica gel

출처 및 근거

ORD 기록
ord-70575816ce5b448e86c03a55f380eb2e
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264448

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