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

HRID 2392195Notes

Reaction equation

HRID 2392195 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-af8dfd8f740b4c57ace898a1ef230f2c
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

Loading…