Sodium hydride → HCID 20636580, compound

HRID 523586Notes

Reaction equation

HRID 523586 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([Cl:14])[CH:9]=1)=[O:6].[H-].[Na+]>C1COCC1>[Cl:14][C:10]1[CH:9]=[C:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 14625246HCID 14625246, compound

Product 1

HCID 20636580HCID 20636580, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(2-chloroethyl)-3-(2-chloro-pyridin-4-yl)urea (I-33a: 7.0 g, 30.042 mmol) in dry THF (40 mL) was reacted with 60% NaH (1.08 g, 45.06 mmol) in dry THF (30 mL) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM) afforded 5.40 g of the product (92% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1% methanol in DCM)

Sources & evidence

ORD record
ord-f7caf8f9f1394a7fa0cfa185266bdc65
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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