HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Chlorosuccinimide → 4-bromo-5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

HRID 1961180
Notes
Print preview

Reaction equation

HRID 1961180 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]([C:21]([OH:23])=[O:22])[S:13][C:14]=1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=1>O1CCCC1>[Br:9][C:10]1[CH:11]=[C:12]([C:21]([OH:23])=[O:22])[S:13][C:14]=1[C:15]1[N:19]([CH3:20])[N:18]=[CH:17][C:16]=1[Cl:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 578265674-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic Acid

Product 1

HCID 578266064-bromo-5-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

N-chlorosuccinimide (NCS) (299 mg, 2.194 mmol) was added in portions to a 30 mL sealed tube reactor containing 4-bromo-5-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (503 mg, 1.23 mmol) in tetrahydrofuran (THF) (6 mL) at room temperature. The mixture was heated to 70° C. for 2 hours. Upon completion, the reaction mixture was partitioned between CHCl3 and H2O, the organic layer dried with Na2SO4, solvents removed by vacuum distillation affording the title compound (0.54 mg, quant.) which was used without further purification. LC-MS (ES) m/z=321 (M+H)+

Workup

  1. customsealed tube reactor
  2. customUpon completion, the reaction mixture 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-827c7bb6bd8a44839ca929074f365bfc
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410158B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes