Phosphorus sulfide (P2S5) → HCID 135786543, compound

HRID 1493021Notes

Reaction equation

HRID 1493021 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[S:20][C:19]([C:21]([NH2:23])=O)=[N:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>O1CCOCC1>[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[S:20][C:19]([C:21](=[S:25])[NH2:23])=[N:18][N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 135786532HCID 135786532, compound

Product 1

HCID 135786543HCID 135786543, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1.5 g (4.5 mmol) of 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2-carboxamide and 1.0 g (2.2 mmol) of P2S5 in 20 ml of dioxane is warmed at reflux for one hour under a nitrogen atmosphere. The reaction is poured through a plug of SiO2, washing with t-butylmethylether. Recrystallization from toluene gives 0.45 g (1.6 g theor., 28%) of the thioamide as a yellow solid, mp 215°-216° C.

Workup

  1. temperatureis warmed
  2. temperatureat reflux for one hour under a nitrogen atmosphere
  3. additionThe reaction is poured through a plug of SiO2
  4. washwashing with t-butylmethylether
  5. customRecrystallization from toluene

Sources & evidence

ORD record
ord-6313e459cd7644f3b1bee1a9d2ade4d6
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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