Sodium Azide → HCID 85903973, compound

HRID 2419374Notes

Reaction equation

HRID 2419374 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl[CH2:6][C:7]([C:9]1[CH:20]=[CH:19][C:12]([S:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)=[O:8]>O.C(Cl)(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:1]([CH2:6][C:7]([C:9]1[CH:20]=[CH:19][C:12]([S:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)=[O:8])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 82165586HCID 82165586, compound

Product 1

HCID 85903973HCID 85903973, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of sodium azide (17.0g.) in water (100ml.) was added to a solution of methyl 4-(chloroacetyl)thiophenoxyacetate (60.1g.) in chloroform (350ml.). Benzyl triethylammonium chloride (300mg.) was then added, and the two phase mixture was shaken for 16 hours. The organic phase was separated, washed with water (2 × 100ml.), dried (MgSO4) and then evaporated in vacuo. The residue was recrystallised from methanol to give methyl 4-(azidoacetyl)thiophenoxyacetate (49.3g.), having a characteristic azide absorption at 2110cm-1 in the infra-red spectrum.

Workup

  1. customThe organic phase was separated
  2. washwashed with water (2 × 100ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was recrystallised from methanol

Sources & evidence

ORD record
ord-d65deef7f71b415e9ee9a1654a51b287
Source dataset
uspto-grants-1978_08
Patent number
US04105790

Reaction notes

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