Ethyl chloroformate → HCID 57471166, compound

HRID 510496Notes

Reaction equation

HRID 510496 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-f3003522b0ba409bb3e77f90ddab9bd3
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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