Chlorosuccinimide → HCID 490381, compound

HRID 732913Notes

Reaction equation

HRID 732913 reaction equation
[Cl:1]N1C(=O)CCC1=O.OCCOCN1C=C(C=C)C(=O)NC1=O.[N-]=[N+]=[N-].[Na+].[OH:28][CH2:29][CH2:30][O:31][CH2:32][N:33]1[CH:40]=[C:39]([CH:41]([N:44]=[N+:45]=[N-:46])[CH2:42]Br)[C:37](=[O:38])[NH:36][C:34]1=[O:35]>COCCOC.O>[OH:28][CH2:29][CH2:30][O:31][CH2:32][N:33]1[CH:40]=[C:39]([CH:41]([N:44]=[N+:45]=[N-:46])[CH2:42][Cl:1])[C:37](=[O:38])[NH:36][C:34]1=[O:35]

Participants

7

Reactant 4

HCID 31398ChlorosuccinimideHCID 33557Sodium AzideHCID 490380HCID 490380, compoundHCID 12081662HCID 12081662, compound

Product 1

HCID 490381HCID 490381, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Chlorosuccinimide (NCS, 88 mg, 0.65 mmol) was added slowly to a precooled (−5° C.) suspension prepared by mixing a solution of 1 (116 mg, 0.55 mmol) in 1,2-dimethoxyethane (20 ml) with a solution of sodium azide (143 mg, 2.2 mmol) in water (0.35 ml). The reaction was stirred for 3 h at 0° C. Completion of the reaction, as described for the isolation of 2a, gave a residue which was purified by silica gel column chromatography. Elution with chloroform:methanol (97:3, v/v) as eluent yielded 2b as a syrup (56 mg, 35%).

Workup

  1. customprepared
  2. customCompletion of the reaction
  3. customgave a residue which
  4. customwas purified by silica gel column chromatography
  5. washElution with chloroform:methanol (97:3

Sources & evidence

ORD record
ord-681376c88d3646049b7ddc6d9f88c267
Source dataset
uspto-grants-2009_09
Patent number
US07589077B2

Reaction notes

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