Sodium Methoxide → HCID 14294243, compound

HRID 2073367Notes

Reaction equation

HRID 2073367 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][N:12]=[N:11][C:10]=2[S:14]CCC(OC)=O)[CH:6]=[CH:7][CH:8]=1.C[O-].[Na+]>CO>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[S:13][N:12]=[N:11][C:10]=2[SH:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14294208HCID 14294208, compound

Product 1

HCID 14294243HCID 14294243, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 11.6 g of 3-[[5-[3-(trifluoromethyl)phenyl]-1,2,3-thiadiazol-4-yl]thio]propanoic acid, methyl ester in 100 ml of dry methanol was treated with 32 ml of 1M methanolic sodium methoxide. After standing one hour, the solvent was removed in vacuo, the residue taken up in dry methanol, filtered and then concentrated. The oil was triturated with ether giving a solid which was collected and dried in vacuo, giving 6.8 g of 5-[3-(trifluoromethyl)phenyl]-1,2,3-thiadiazole-4-thiol, monosodium salt as a yellow powder, mp>200° C.

Workup

  1. customthe solvent was removed in vacuo
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe oil was triturated with ether giving a solid which
  5. customwas collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-467fee57e17842178bbcc6ddc170c10d
Source dataset
uspto-grants-1990_04
Patent number
US04916237

Reaction notes

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