Dimethylformamide → HCID 20331942, compound

HRID 1764772Notes

Reaction equation

HRID 1764772 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9](=[S:10])[NH:8][N:7]=[N:6]1.CN(C)C=O.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1>CC(C)=O>[NH2:2][CH2:3][CH2:4][N:5]1[C:9]([S:10][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[N:8][N:7]=[N:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 178479233HCID 178479233, compound

Product 1

HCID 20331942HCID 20331942, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 22.8 g. (12.5 mmol) of 1-(2-aminoethyl)-1,4-dihydro-5H-tetrazole-5-thione, hydrochloride in 100 ml. of N,N-dimethylformamide and 100 ml. of acetone was added 34.3 ml. (25 mmol) of triethylamine. To the resulting suspension was added slowly a solution of 19.5 g. (12.5 mmol) of p-methoxybenzyl chloride in 30 ml. of acetone. After stirring at room temperature for 15 hours, the mixture was filtered. The filtrate was evaporated to dryness. The residue was taken up in 350 ml. of 5% NaHCO3, and extracted with ethyl acetate. The combined extract was dried (MgSO4) and evaporated to dryness to give an oil which was chromatographed on a silica gel column, eluting with a gradient of 5-10% ethanol in chloroform. Fractions containing product by thin layer chromatography were pooled, and evaporated to dryness to give 1-(2-aminoethyl)-5-(4-methoxybenzylthio)-1H-tetrazole as a brown oil (26 g., 80%). An analytical sample of the crystalline amine hydrochloride (mp 148°-150°) was obtained by treating the product with an ethereal HCl solution.

Workup

  1. additionTo the resulting suspension was added slowly a solution of 19.5 g
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. extractionof 5% NaHCO3, and extracted with ethyl acetate
  5. extractionThe combined extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated to dryness
  8. customto give an oil which
  9. customwas chromatographed on a silica gel column
  10. washeluting with a gradient of 5-10% ethanol in chloroform
  11. additionFractions containing product by thin layer chromatography
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-fa3322653aba400696268ff9a5e2ca5d
Source dataset
uspto-grants-1978_09
Patent number
US04117125

Reaction notes

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