Thiophenol → HCID 15480823, compound

HRID 1857359Notes

Reaction equation

HRID 1857359 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Br[CH2:16][C:17]1[N:22]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:21](=[O:29])[C:20]([Cl:30])=[N:19][CH:18]=1>C(Cl)Cl>[Cl:30][C:20]1[C:21](=[O:29])[N:22]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:17]([CH2:16][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 15480822HCID 15480822, compound

Product 1

HCID 15480823HCID 15480823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

THIOPHENOL (1.28 ML, 12.5 MMOL) WAS ADDED DROPWISE TO A STIRRED SOLUTION OF TRIETHYLAMINE (3.0 ML, 21.5 MMOL) AND 6-BROMOMETHYL-3-CHLORO-1-ETHOXYCARBONYLMETHYLPYRAZINONE (3.86 G, 12.5 MMOL) IN METHYLENE CHLORIDE (20 ML). AFTER 15 MIN THE MIXTURE WAS PARTITIONED BETWEEN METHYLENE CHLORIDE AND WATER. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID WHICH WAS CARRIED FORWARD TO THE NEXT STEP:

Workup

  1. customAFTER 15 MIN THE MIXTURE WAS PARTITIONED BETWEEN METHYLENE CHLORIDE AND WATER
  2. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  3. customEVAPORATED IN VACUO

Sources & evidence

ORD record
ord-6ce8584401f54452a474aa26a708df80
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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