Sodium hydride → HCID 72429334, compound

HRID 349609

Reaction equation

HRID 349609 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[NH:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[H-].[Na+].[Cl:18][CH:19]=[CH:20][CH2:21]Cl>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[N:4]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:21][CH:20]=[CH:19][Cl:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 3571360N-(tert-Butoxycarbonyl)-2-bromoaniline

Product 1

HCID 72429334HCID 72429334, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3.2 (350 mg, 1.29 mmol) in DMF (7 ml) was cooled to 0° C. and NaH (93 mg, 3.85 mmol) was added. The resulting mixture was stirred for 15 mins and 1,3 dichloropropene (358 μl, 3.85 mmol) was added. The mixture was allowed to warm to 25 ° C. and stirred for 15 h. The mixture was then concentrated. H2O (10 ml) was added to the residue and the solution was extracted with EtOAc (3×10 ml). The combined organic layers were dried with MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9) to afford 3.3 (400 mg, 89%) as a pale yellow oil. FABMS (NBA/NaI) 346 (M+H+ expected 346).

Workup

  1. stirringstirred for 15 h
  2. concentrationThe mixture was then concentrated
  3. additionH2O (10 ml) was added to the residue
  4. extractionthe solution was extracted with EtOAc (3×10 ml)
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, EtOAc/Hex 1:9)

Sources & evidence

ORD record
ord-524453802d4c4ea4bede5730af445a25
Source dataset
uspto-grants-2007_02
Patent number
US07179921B2

Linked notes

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