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

HRID 1845598Notes

Reaction equation

HRID 1845598 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-46ed57324dcc4b2ea53e8f7637cbe007
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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