Chlorosuccinimide → HCID 9964518, compound

HRID 1432879Notes

Reaction equation

HRID 1432879 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Cl:13]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:13][C:5]1[S:1][C:2]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11321378Ethyl 2-thienyloxyacetate

Product 1

HCID 9964518HCID 9964518, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of ethyl 2-thienyloxyacetate (1.1 g, 5.9 mmol) in acetic acid (15 mL) is added N-chlorosuccinimide (0.78 g, 5.9 mmol). The solution is stirred for 1.5 hour. After this time the solution is concentrated. The resulting oil is dissolved in ether and washed with 1N NaOH, water and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated under vacuum. The title compound (1.26 g, 5.7 mmol) is obtained as an oil. 1H NMR (CDCl3, 300 MHz) δ6.52 (d, 1H), 6.06 (d, 1H), 4.60 (s, 2H), 4.24 (q, 2H), 1.31 (t, 3H).

Workup

  1. concentrationAfter this time the solution is concentrated
  2. dissolutionThe resulting oil is dissolved in ether
  3. washwashed with 1N NaOH, water and sat. NaCl
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1ca2664e99204126ab2b62c4df37e9a7
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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