Diethyl Ether → HCID 20332972, compound

HRID 1706981Notes

Reaction equation

HRID 1706981 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N:13]1[C:17]([CH2:18][N:19]([CH3:21])[CH3:20])=[N:16][C:15]([C:22]([NH2:24])=O)=[N:14]1)=[O:5].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.CCOCC>N1C=CC=CC=1.CN(C)C=O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N:13]1[C:17]([CH2:18][N:19]([CH3:21])[CH3:20])=[N:16][C:15]([C:22]#[N:24])=[N:14]1)=[O:5]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 128317381-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide

Product 1

HCID 20332972HCID 20332972, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.18 g (0.01 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxamide and 2.86 g (0.015 mole) of p-toluenesulphonic acid chloride in 2.42 ml of pyridine and 24 ml of N,N-dimethylformamide is stirred for 2 hours at room temperature. The initially yellow colour of the reaction mixture changes during this time to green and then to red-brown. The reaction solution is poured into ice water, and extraction is performed twice with ether. The organic phase is washed three times with water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo to dryness. The residue is crystallised from isopropanol. After filtration with suction followed by drying, there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carbonitrile, m.p. 117°-119°.

Workup

  1. washThe organic phase is washed three times with water
  2. dry with materialit is dried over sodium sulphate
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue is crystallised from isopropanol
  5. filtrationAfter filtration with suction
  6. customby drying

Sources & evidence

ORD record
ord-8ffe0a9bc2e64235b3b2efaebc255674
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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