Water → HCID 67938383, compound

HRID 1198914Notes

Reaction equation

HRID 1198914 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[N:7]1([CH2:13][CH2:14][NH:15][C:16](=[O:32])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH2:26][NH:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:21][CH:20]=2)[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.C(=O)(O)[O-].[Na+].O>O1CCCC1>[OH2:3].[CH2:5]([O:4][C:2]([N:10]1[CH2:9][CH2:8][N:7]([CH2:13][CH2:14][NH:15][C:16](=[O:32])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH2:26][NH:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:23][CH:24]=2)[CH2:12][CH2:11]1)=[O:3])[CH3:6].[CH2:5]([O:4][C:2]([N:10]1[CH2:9][CH2:8][N:7]([CH2:13][CH2:14][NH:15][C:16](=[O:32])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH2:26][NH:27][C:28](=[O:31])[NH:29][N:30]=3)=[CH:23][CH:24]=2)[CH2:12][CH2:11]1)=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 14099038HCID 14099038, compound

Product 1

HCID 67938383HCID 67938383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.15 ml of ethyl chloroformate were added, whilst ice-cooling, to a mixture of 0.360 g of N-[2-(1-piperazinyl)ethyl]-α-[4-(2,3,4,5-tetrahydro-3-oxo-1,2,4-triazin-6-yl)phenoxy]acetamide [prepared as described in step (a) above], 0.13 g of sodium bicarbonate, 10 ml of water and 50 ml of tetrahydrofuran, and the mixture was stirred for 30 minutes. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluent: a 1:1 by volume mixture of ethanol and methylene chloride), followed by recrystallization from ethanol, to give 0.264 g of the title compound as colorless fine crystals melting at 200°-240° C. (with decomposition).

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography through silica gel (eluent
  3. additiona 1:1 by volume mixture of ethanol and methylene chloride),
  4. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-ecbb451d0848483e86c9f41bd929c4fa
Source dataset
uspto-grants-1990_02
Patent number
US04898862

Reaction notes

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