1-Bromo-2-methylpropane → HCID 15295335, compound

HRID 128574Notes

Reaction equation

HRID 128574 reaction equation
[S:1]1(=[O:15])(=[O:14])[C:6]2[S:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:5]=2[CH:4]=[N:3][NH:2]1.[H-].[Na+].[CH3:18][CH:19]([CH3:22])[CH2:20]Br>CN(C=O)C.O>[CH3:18][CH:19]([CH3:22])[CH2:20][N:2]1[N:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([NH2:13])(=[O:11])=[O:12])[S:7][C:6]=2[S:1]1(=[O:14])=[O:15]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 19374697HCID 19374697, compound

Product 1

HCID 15295335HCID 15295335, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The product from step C (0.05 g, 0.18 mmol) was dissolved in DMF (1 mL). Sodium hydride (0.016 g, 40 mmol of a 60% suspension in mineral oil) was added slowly at room temperature. The mixture was stirred for 15 min and then 2-methylbromopropane (0.024 mL, 0.40 mmol) was added. The mixture was warmed to 60° C. and stirred for 12h. DMF was evaporated under high vacuum. The residue obtained was diluted with water (1 mL) and the mixture was extracted with ethyl acetate (3×1 mL). The combined extracts were dried over MgSO4 and evaporated to provide an oil which was purified by flash column chromatography (silica, hexane-ethyl acetate gradient) to give the desired compound as a white solid, crystallization in ethyl acetate-hexane gave 0.032 g (52%). mp:130°-132° C. 1HNMR (CDCl3):δ:0.96 (6H, d, 2CH3); 2.18 (1H, m, CH); 3.78 (2H, d, CH2); 5.27 (2H, s, NH2 exchangeable); 7.67 (1H, 1s, CH); 7.91 (1H, s, CH=N). Analysis calculated for C9H13N3O4S3 : C, 33.42; H, 4.05; N, 12.99. Found: C, 33.51; H, 4.04; N, 12.91.

Workup

  1. stirringstirred for 12h
  2. customDMF was evaporated under high vacuum
  3. customThe residue obtained
  4. extractionthe mixture was extracted with ethyl acetate (3×1 mL)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. customevaporated
  7. customto provide an oil which
  8. customwas purified by flash column chromatography (silica, hexane-ethyl acetate gradient)
  9. customto give
  10. customthe desired compound as a white solid, crystallization in ethyl acetate-hexane
  11. customgave 0.032 g (52%)

Sources & evidence

ORD record
ord-05f8737499bb4833bd217e02e0ff164c
Source dataset
uspto-grants-1995_11
Patent number
US05464831

Reaction notes

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