Morpholine → HCID 53701460, compound

HRID 1706992Notes

Reaction equation

HRID 1706992 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10]I)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CO>[CH3:1][O:2][C:3]([C:5]1[N:9]=[C:8]([CH2:10][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[N:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[N:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 54482160HCID 54482160, compound

Product 1

HCID 53701460HCID 53701460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 38.7 g (0.075 mole) of 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(iodomethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester and 13.1 g (0.150 mole) of morpholine in 750 ml of methanol is stirred for 8 hours at 40°. The reaction mixture is then concentrated in vacuo; water is added to the residue and extraction is performed twice with methylene chloride. The organic phase is washed three times with water and twice with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo. The residue is triturated with ether, whereupon the reaction product is obtained in crystalline form. After filtration with suction and drying in vacuum, there is obtained 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(morpholinomethyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester, m.p. 141°-143°.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. additionwater is added to the residue and extraction
  3. washThe organic phase is washed three times with water
  4. dry with materialit is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated with ether, whereupon the reaction product
  7. customis obtained in crystalline form
  8. filtrationAfter filtration with suction
  9. customdrying in vacuum

Sources & evidence

ORD record
ord-5a0d9b9f1c8344fb8ade7422e8e981de
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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