Sodium Azide → HCID 11439747, compound

HRID 1435696Notes

Reaction equation

HRID 1435696 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[N:9]=[C:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[CH3:24])(=[O:16])=[O:15])[S:11][CH:12]=1)(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>C(O)C>[N:25]([CH2:6][CH2:7][C:8]1[N:9]=[C:10]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=2[CH3:24])(=[O:16])=[O:15])[S:11][CH:12]=1)=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 87545953HCID 87545953, compound

Product 1

HCID 11439747HCID 11439747, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of EXAMPLE 191A (1.00 g, 2.43 mmol) and sodium azide (791 mg, 12.17 mmol) in ethanol (30 mL) was refluxed for 2.5 h. The solvent was evaporated and the crude material was extracted with ethyl acetate. The organic phase was dried (Sodium sulfate) and the solvent was evaporated. The crude product was purified by flash column chromatography on silica gel eluting with 2-5% acetone in DCM to yield the title product (633 mg, 1.77 mmol, 70%): MS (Ionspray, [M+H]+) m/z 357.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude material was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Sodium sulfate)
  4. customthe solvent was evaporated
  5. customThe crude product was purified by flash column chromatography on silica gel eluting with 2-5% acetone in DCM

Sources & evidence

ORD record
ord-b003f1e27c524b0ea57ad923d0d00a05
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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