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

HRID 1591105Notes

Reaction equation

HRID 1591105 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2cd26fdbd710416cb7994ab148f63c22
Source dataset
uspto-grants-1993_04
Patent number
US05206259

Reaction notes

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