Chlorosuccinimide → methyl 4-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

HRID 1961228Notes

Reaction equation

HRID 1961228 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[CH3:9][N:10]1[C:14]([C:15]2[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[S:18][CH:19]=2)=[C:13]([CH3:24])[CH:12]=[N:11]1>O1CCCC1>[Cl:8][C:12]1[C:13]([CH3:24])=[C:14]([C:15]2[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[S:18][CH:19]=2)[N:10]([CH3:9])[N:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 57826420methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

Product 1

HCID 57826401methyl 4-(3-chloro-1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

NCS (1.78 g, 13.09 mmol) was added in portions to a 125 mL sealed tube reactor containing methyl 4-(1,4-dimethyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (2.07 g, 8.76 mmol) in Tetrahydrofuran (THF) (40 ml) at room temperature. The mixture was heated to 100° C. for 1 hour. Upon completion the product was partitioned between CHCl3 and H2O, the organic layer dried with Na2SO4, solvents removed by vacuum distillation affording the title compound (2.18 g, 7.97 mmol, 91%) which was used without further purification: LC-MS (ES) m/z=271 (M+H)+.

Workup

  1. customsealed tube reactor
  2. customUpon completion the product was partitioned between CHCl3 and H2O
  3. dry with materialthe organic layer dried with Na2SO4, solvents
  4. customremoved by vacuum distillation

Sources & evidence

ORD record
ord-7b691d1ef7f04499929fd65e4f84ccc2
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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