Calcium Carbonate → HCID 54291268, compound

HRID 1583874Notes

Reaction equation

HRID 1583874 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[NH2:14])[O:7][CH:8](O)[CH3:9])([O-:3])=[O:2].C(=O)([O-])[O-:16].[Ca+2].Cl[C:21]([O:23][CH2:24][CH2:25][Cl:26])=[O:22]>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([O:7][CH2:8][CH2:9][OH:16])[CH:11]=[CH:12][C:13]=1[NH:14][C:21](=[O:22])[O:23][CH2:24][CH2:25][Cl:26])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 123052-Chloroethyl chloroformateHCID 22734874HCID 22734874, compound

Product 1

HCID 54291268HCID 54291268, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4 mols (792 g) of 3-nitro-4-aminophenoxyethanol are dissolved in 1,600 ml of dioxane. 2.4 mols (240 g) of calcium carbonate are added. The temperature is raised to about 90° C. and 4.8 mols (686 g) of β-chloroethyl chloroformate are then introduced gradually, whilst stirring. When the addition has ended, heating is maintained for 30 minutes at 90° C. The reaction medium is filtered hot. The cooled filtrate is diluted with petroleum ether to precipitate the desired product, which, after recrystallisation from dioxane and drying in vacuo, melts at 119° C.

Workup

  1. additionWhen the addition
  2. temperatureheating
  3. temperatureis maintained for 30 minutes at 90° C
  4. filtrationThe reaction medium is filtered hot
  5. additionThe cooled filtrate is diluted with petroleum ether
  6. customto precipitate the desired product, which
  7. customafter recrystallisation from dioxane
  8. customdrying in vacuo, melts at 119° C.

Sources & evidence

ORD record
ord-838f41d12c144fe4bb40c37adcfbc97a
Source dataset
uspto-grants-1985_11
Patent number
US04555247

Reaction notes

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