p-Chlorothiophenol → HCID 58579932, compound

HRID 2059854Notes

Reaction equation

HRID 2059854 reaction equation
O[CH2:2][C:3]1[CH:4]=[N:5][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7](=[O:9])[CH:8]=1.CCN(CC)CC.CS(Cl)(=O)=O.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([SH:36])=[CH:32][CH:31]=1>C(Cl)Cl>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36][CH2:2][C:3]2[CH:4]=[N:5][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7](=[O:9])[CH:8]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58579849HCID 58579849, compound

Product 1

HCID 58579932HCID 58579932, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 4-(hydroxymethyl)-6-oxopyridazine-1(6H)-carboxylate Part B (185 mg, 0.82 mmol) and Et3N (0.34 mL, 2.45 mmol) in CH2Cl2 (5 mL) under nitrogen at −10° C. was added a solution of methanesulfonyl chloride (0.076 mL, 0.98 mmol) in CH2Cl2 (2 mL). After stirring at RT for 15 min, 4-chlorobenzenethiol (355 mg, 2.45 mmol) was added to the reaction and the stirring at RT continued for 3 days. Following removal of the volatiles under vacuum, the crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 50:50 gradient, using LC-MS to identify fractions containing the desired product) to afford tert-butyl 4-((4-chlorophenylthio)methyl)-6-oxopyridazine-1(6H)-carboxylate 7C (137 mg, 47% yield).

Workup

  1. waitthe stirring at RT continued for 3 days
  2. customremoval of the volatiles under vacuum
  3. customthe crude product was purified by flash chromatography (silica gel/hexane-EtOAc 100:0 to 50:50 gradient
  4. additioncontaining the desired product)

Sources & evidence

ORD record
ord-88765b7a26a249e780968736c6809564
Source dataset
uspto-grants-2012_10
Patent number
US08278316B2

Reaction notes

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