Thionyl Chloride → HCID 20505547, compound

HRID 355232Notes

Reaction equation

HRID 355232 reaction equation
[N:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].S(Cl)([Cl:16])=O>C(Cl)Cl.CN(C=O)C>[N:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 205054704-(Azidomethyl)benzoic acid

Product 1

HCID 20505547HCID 20505547, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of p-azidomethylbenzoic acid (1.063 g, 6.00 mmol) in CH2Cl2 (60 ml) at room temperature were added dropwise thionyl chloride (1 ml, excess) and DMF (5 drops). The mixture was stirred at room temperature for 2.5 h and evaporated, yielding 1.13 g of title compound as a light yellow oil: 1Hmr (CDCl3) δ: 4.48 (2H, s, --CH2N3), 7.38-7.52-8.07-8.22 ppm (4H, A2 'B2 ', aromatic Hs); ir (neat) νmax : 2090 (--N3) and 1750 cm-1 (br. --COCl). This material was used in the next step without further purification.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-e143439fcdcf4b0aa1c6188a3fe919c8
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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