1-Bromo-2-methylpropane → HCID 15295336, compound

HRID 128576Notes

Reaction equation

HRID 128576 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[S:5](=[O:16])(=[O:15])[NH:4][N:3]=1.[H-].[Na+].[CH3:19][CH:20]([CH3:23])[CH2:21]Br>CN(C=O)C.O>[CH3:1][C:2]1[C:7]2[CH:8]=[C:9]([S:11]([NH2:14])(=[O:12])=[O:13])[S:10][C:6]=2[S:5](=[O:16])(=[O:15])[N:4]([CH2:19][CH:20]([CH3:23])[CH3:21])[N:3]=1

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 19374696HCID 19374696, compound

Product 1

HCID 15295336HCID 15295336, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The product from step B (0.9 g, 2.85 mmol) was dissolved in DMF (10 mL). Sodium hydride (0.17 g, 4.28 mmol of a 60% suspension in mineral oil) was added slowly at room temperature. The mixture was stirred for 15 min and then 2-methyl bromopropane (0.47 mL, 4.28 mmol) was added. The mixture was warmed to 80° C. and stirred for 2h. And then cooled to 0° C. and stirred for 12h. DMF was evaporated under high vacuum. The residue obtained was diluted with water (20 mL) and extracted with ethyl acetate (3×20 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 (0.54 g, 50%). mp: 140°-142° C. 1H NMR (DMSO-d6): δ:0.89 (6H, d, 2CH3); 2.03 (1H, m, CH); 2.49 (3H, s, CH3); 3.64 (2H, δ, CH2); 7.94 (1H, s, CH); 8.21 (2H, s, NH2 exchangeable). Analysis calculated for C9H13N3O4S3 : C, 35.59; H, 4.78; N, 12.45 Found: C, 35.56; H, 4.44; N, 12.36.

Workup

  1. stirringstirred for 2h
  2. temperatureAnd then cooled to 0° C.
  3. stirringstirred for 12h
  4. customDMF was evaporated under high vacuum
  5. customThe residue obtained
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialThe combined extracts were dried over MgSO4
  8. customevaporated
  9. customto provide an oil which
  10. customwas purified by flash column chromatography (silica, hexane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-11e68de2b53b40dca2741e06f5496113
Source dataset
uspto-grants-1995_11
Patent number
US05464831

Reaction notes

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