Ethyl chloroformate → HCID 13365015, compound

HRID 1154563Notes

Reaction equation

HRID 1154563 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[CH2:7]1[O:22][CH:10]([C:11]2[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=2[NH2:21])[O:9][CH2:8]1.[OH-].[Na+]>O1CCCC1.O>[CH2:8]1[O:9][CH:10]([C:11]2[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:12]=2[NH:21][C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:22][CH2:7]1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 133650142-(1,3-Dioxolan-2-yl)-3,4-dimethoxyaniline

Product 1

HCID 13365015HCID 13365015, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethylchloroformate (1.9 g, 17.5 mM) is added with stirring to 2-amino-5,6-dimethoxybenzaldehyde-ethyleneketal (1.6 g, 7.1 mM) dissolved in tetrahydrofuran (50 ml). A solution of sodium hydroxide in H2O (0.72 g in 3.5 ml H2O) is added and the resulting solution is stirred for 2 hours at room temperature. The tetrahydrofuran is removed in vacuo and the residue extracted with CHCl3 (2×100 ml). The extracts are dried over Na2SO4, filtered, and the solvent removed in vacuo. The crude product is recrystallized from n-hexane; yield 1.2 g (57.1%); m.p. 95°-96° C.

Workup

  1. customThe tetrahydrofuran is removed in vacuo
  2. extractionthe residue extracted with CHCl3 (2×100 ml)
  3. dry with materialThe extracts are dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe crude product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-a156320aa65b4b14b1e5a40d778261d1
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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