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

Reaktionsgleichung

Reaktionsgleichung von HRID 257856
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70575816ce5b448e86c03a55f380eb2e
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264448

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