Sodium Hydroxide → 3,4-Dichloro-N-[3-(1H-1,2,4-triazol-1-yl)propyl]benzamide

HRID 1589166Notes

Reaction equation

HRID 1589166 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[N:4][CH:3]=[N:2]1.[OH-].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:16](Cl)=[O:17]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[Cl:22])[C:16]([NH:9][CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 43796821H-1,2,4-Triazole-1-propanamine

Product 1

HCID 135888673,4-Dichloro-N-[3-(1H-1,2,4-triazol-1-yl)propyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of about 3.78 g of 1H-1,2,4-triazole-1-propanamine and about 33 ml of approximately 1N sodium hydroxide in about 100 ml of methylene chloride was stirred. An about 6.9 g portion of 3,4-dichlorobenzoyl chloride was added, the mixture was stirred about 6 hours, then allowed to stand overnight. An about 10 ml portion of approximately 1N sodium hydroxide and about 100 ml of methylene chloride were added and the mixture was shaken, then allowed to separate. The organic layer was washed with two about 40 ml portions of water, dried, filtered and evaporated to a solid which was crystallized from ethyl acetate, giving about 5.0 g of the desired product as off-white crystals, mp 128°-130° C.

Workup

  1. stirringthe mixture was stirred about 6 hours
  2. stirringthe mixture was shaken
  3. customto separate
  4. washThe organic layer was washed with two about 40 ml portions of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to a solid which
  8. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-bad97414b51d49edbe16ab86835e1a37
Source dataset
uspto-grants-1986_02
Patent number
US04568685

Reaction notes

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