Triethylamine → HCID 178513356, compound

HRID 1821967Notes

Reaction equation

HRID 1821967 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])[CH:18]=[C:17]([Cl:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.Cl.[NH2:29][OH:30].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:20]=[C:19]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])[CH:18]=[C:17]([Cl:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:29][OH:30])=[NH:14])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86602296HCID 86602296, compound

Product 1

HCID 178513356HCID 178513356, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 g of 4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-benzonitrile, 247 mg of hydroxylamine hydrochloride and 430 mg of triethylamine are stirred for 48 hours at 80° C. in 25 ml of ethanol. The reaction mixture is poured onto water and extracted with ethyl acetate. Concentration of the organic phase and crystallisation from diethyl ether yield 4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-N-hydroxy-benzamidine having a melting point of 144-146° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with ethyl acetate
  3. customConcentration of the organic phase and crystallisation from diethyl ether

Sources & evidence

ORD record
ord-fcea1344a17d435d98427652c538580a
Source dataset
uspto-grants-2009_10
Patent number
US07608631B2

Reaction notes

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