Water → HCID 14249914, compound

HRID 867748Notes

Reaction equation

HRID 867748 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6](Cl)[CH3:7])=[CH:2]1.[N-:9]=[N+:10]=[N-:11].[Na+].O>CN(C=O)C>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([N:9]=[N+:10]=[N-:11])[CH3:7])=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 14249911HCID 14249911, compound

Product 1

HCID 14249914HCID 14249914, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(thien-3-yl)chloroethane (5.0 g, 34 mmol) and sodium azide (2.65 g, 41 mmol) in DMF was stirred at room temperature for three days. The reaction mixture was poured into H2O (500 ml) and extracted with CH2Cl2 (3×200 ml). The organic extracts were washed with H2O (5×100 ml), dried over MgSO4 and concentrated in vacuo to give the product (5.02 g, 96% yield) as a brown oil; IR (neat) 2110 cm-1 ; 1H NMR (CDCl3) δ1.55 (d, J=7 Hz, 3H, CHCH3), 4.67 (q, J=7 Hz, 1H, CHCH3), 6.98-7.43 (m, 3H, thiophene-H).

Workup

  1. extractionextracted with CH2Cl2 (3×200 ml)
  2. washThe organic extracts were washed with H2O (5×100 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f21e9b9ac4ff4baf89177525c708cff1
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

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