Chloroacetyl chloride → 3-[5-(Chloromethyl)-1,2,4-oxadiazol-3-yl]benzonitrile

HRID 732011Notes

Reaction equation

HRID 732011 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][OH:9])=[NH:7])#[N:2].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=O>ClCCl>[Cl:20][CH2:21][C:22]1[O:9][N:8]=[C:6]([C:5]2[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=2)[C:1]#[N:2])[N:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178509779HCID 178509779, compound

Product 1

HCID 578379493-[5-(Chloromethyl)-1,2,4-oxadiazol-3-yl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-cyano-N-hydroxy-benzamidine (1.0 g, 6.2 mmol), triethylamine (1.5 ml, 10.6 mmol) and chloroacetyl chloride (0.74 ml, 9.3 mmol) in dichloromethane (12 ml). Purification was performed by decolorizing with silica gel. 1H NMR (CDCl3), d (ppm): 8.40 (s, 1H), 8.32 (d, 1H), 7.82 (d, 1H), 7.64 (t, 1H), 4.77 (s, 2H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-8fb32350b59d400b97055886c8199f4a
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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