Methanol → HCID 178419748, compound

HRID 2413336Notes

Reaction equation

HRID 2413336 reaction equation
[CH2:1]([Br:10])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].C[Si](C)(C)[N:13]1[CH:17]=[N:16][C:15]([S:18][Si](C)(C)C)=[N:14]1.CO>C(#N)C.CN(C)P(=O)(N(C)C)N(C)C>[BrH:10].[CH2:1]([S:18][C:15]1[N:16]=[CH:17][NH:13][N:14]=1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 887MethanolHCID 6259Phenacyl bromideHCID 204308151-(Trimethylsilyl)-3-[(trimethylsilyl)sulfanyl]-1H-1,2,4-triazole

Product 1

HCID 178419748HCID 178419748, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

1.62 g (8.1 mmoles) of phenacyl bromide were added to a solution of 1.90 g (7.76 mmoles) of 1-trimethylsilyl-3-trimethylsilylthio-1H-1,2,4-triazole in 10 ml of acetonitrile and 1.55 ml of hexamethylphosphoric triamide and the reaction was complete after stirring for 15 minutes at room temperature. The precipitate formed after the addition of 4 ml of methanol was filtered off and was washed with diethyl ether and with hexane to obtain a yield of 1.85 g (79.5%) of 3-phenacylthio-1H-1,2,4-triazole hydrobromide melting at 201.5°-202° C. (dec.). A second crop of 0.3 g (13%) melting at 191°-192° C. (dec.)) was isolated from the mother liquor. 0.90 g of this salt was taken up in 10 ml of water which was layered with 20 ml of ethyl acetate. The pH was adjusted to 9 with 1N potassium hydroxide and the free base was extracted from the water layer with ethylacetate to obtain 0.66 g (100% yield) of 3-phenacylthio-1H-1,2,4-triazole melting at 119°-120° C. Crystallization from ethyl acetate raised the melting point to 120°-121° C.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwas washed with diethyl ether and with hexane

Sources & evidence

ORD record
ord-8158326dd9b649edb93f8a3d2a9c14a6
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Reaction notes

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