Ethyl chloroformate → HCID 57471166, compound

HRID 1044478Notes

Reaction equation

HRID 1044478 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][CH2:9][CH:8]1[NH2:19].[CH2:24]([O:26][C:27](Cl)=[O:28])[CH3:25]>N1C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:6][CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][CH2:9][CH:8]1[NH:19][C:27](=[O:28])[O:26][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 57467188HCID 57467188, compound

Product 1

HCID 57471166HCID 57471166, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1-(3,4-dichlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine hydrochloride (1.95 g, 5.80 mmol) in pyridine 10 ml) the ethylchloroformate (1.00 g, 9.28 mmol) was added slowly under nitrogen. The mixture was stirred over night at RT. The solvent was reduced under vacuo and extracted with CH2Cl2 after addition of HCl (1N). The organic layer was washed with HCl (1N), NaHCO3 solution, and NaCl solution, then dried on MgSO4 and the solvent was removed. The product was obtained as an orange oil that precipitates after a few hours (2.10 g, 5.14 mmol, 89%).

Workup

  1. extractionextracted with CH2Cl2
  2. additionafter addition of HCl (1N)
  3. washThe organic layer was washed with HCl (1N), NaHCO3 solution, and NaCl solution
  4. customdried on MgSO4
  5. customthe solvent was removed
  6. customThe product was obtained as an orange oil
  7. customthat precipitates after a few hours (2.10 g, 5.14 mmol, 89%)

Sources & evidence

ORD record
ord-d030d44b4d904fcfac76d117a657a7c8
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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