Triethylamine → HCID 14099148, compound

HRID 568309Notes

Reaction equation

HRID 568309 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[N:5]=[N:4][CH:3]=1.C(N(CC)CC)C.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>O1CCCC1.C(Cl)(Cl)Cl>[Cl:8][C:7]1[C:2]([NH:1][C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:3][N:4]=[N:5][C:6]=1[Cl:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 64032025,6-dichloropyridazin-4-amine

Product 1

HCID 14099148HCID 14099148, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of 2.0 grams (0.012 mole) of 4-amino-5,6-dichloropyridazine in 75 ml of tetrahydrofuran is cooled to 0° C. and 1.5 grams (0.015 mole) of triethylamine is added in one portion. A solution of 2.3 grams (0.015 mole) of phenyl chloroformate in tetrahydrofuran is added dropwise during a 30 minute period. Upon completion of addition the reaction mixture is allowed to warm to ambient temperature where it is stirred for three days. The reaction mixture is taken up in 500 ml of chloroform and filtered to collect 0.98 gram of phenyl N-(5,6-dichloro-4-pyridazinyl)carbamate. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel to yield an additional 0.9 gram of phenyl N-(5,6-dichloro-4-pyridazinyl)carbamate.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureto warm to ambient temperature where it
  3. filtrationfiltered
  4. customto collect 0.98 gram of phenyl N-(5,6-dichloro-4-pyridazinyl)carbamate
  5. concentrationThe filtrate is concentrated under reduced pressure to a residue

Sources & evidence

ORD record
ord-29e4c381e0664089b140c5a870c3b051
Source dataset
uspto-grants-1988_03
Patent number
US04728355

Reaction notes

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