Hydrochloric Acid → (4-Chloro-benzylidene)-[5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-amine

HRID 1823850Notes

Reaction equation

HRID 1823850 reaction equation
[C:1]([NH:3][C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[Cl:11])=[O:5])#[N:2].[N:12]#CN.Cl[C:16]1[CH:20]=[CH:19]S[C:17]=1[C:21]([Cl:23])=O.Cl.C(O[CH2:28][CH3:29])C>[OH-].[Na+]>[Cl:23][C:21]1[CH:29]=[CH:28][C:20]([CH:19]=[N:2][C:1]2[N:3]=[C:4]([C:6]3[S:7][CH:8]=[CH:9][C:10]=3[Cl:11])[O:5][N:12]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 9864CyanamideHCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 23570762N-cyano-3-chloro-thiophene-2-carboxylic acid amide

Product 1

HCID 69088885(4-Chloro-benzylidene)-[5-(3-chloro-thiophen-2-yl)-[1,2,4]-oxadiazol-3-yl]-amineYield 75%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

N-Cyano-3-chloro-thiophene-2-carboxylic acid amide: To a solution of cyanamide (302.4 mg, 7.2 mmol) in 10% aqueous sodium hydroxide (3 mL) was added 3-chloro-thiophene-2-carbonyl chloride (1.09 g, 6 mmol) in diethyl ether (3 mL). It was stirred for 1 h and acidified with 1N HCl to give precipitates, which was collected by filtration, then washed with water to yield 807 mg (75%) of the title compound.

Workup

  1. customto give
  2. customprecipitates
  3. filtrationwhich was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-acdc7e5d2f8e45288a5e4675f8b69c07
Source dataset
uspto-grants-2006_05
Patent number
US07041685B2

Reaction notes

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