Hydrochloric Acid → isobutyl N-(5-chloro-3-methoxypyrazin-2-yl)carbamate

HRID 1378353Notes

Reaction equation

HRID 1378353 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[NH2:9][C:10]1[C:15]([O:16][CH3:17])=[N:14][C:13]([Cl:18])=[CH:12][N:11]=1.N1C=CC=CC=1.Cl>ClCCl>[Cl:18][C:13]1[N:14]=[C:15]([O:16][CH3:17])[C:10]([NH:9][C:2](=[O:3])[O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049Pyridine2×HCID 62365Isobutyl chloroformate2×HCID 107970362-Amino-5-chloro-3-methoxypyrazine

Product 1

HCID 22911289isobutyl N-(5-chloro-3-methoxypyrazin-2-yl)carbamateYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (4.1 g) was added to a solution of 2-amino-5-chloro-3-methoxypyrazine (4.8 g) and pyridine (2.37 g) in dichloromethane (50 ml). The solution was left to stand for 20 hours and then two further portions of isobutyl chloroformate (1.02 g) and pyridine (0.59 g) were added at 2 hour intervals. 2M hydrochloric acid (25 ml) was added and the organic layer was separated. The solution was washed with 2M hydrochloric acid (2×25 ml), water (25 ml) and saturated sodium chloride solution (25 ml) The solution was dried (MgSO4) and volatile material was removed by evaporation. The residue was recrystallised from isohexane to give isobutyl N-(5-chloro-3-methoxypyrazin-2-yl)carbamate (6.15 g), m.p. 90°-91° C.; microanalysis found: C, 46.3; H, 5.5; N, 16.4%; C10H14C1N3O3 requires: C, 46.3; H, 5.4; N, 16.2%.

Workup

  1. waitThe solution was left
  2. customthe organic layer was separated
  3. washThe solution was washed with 2M hydrochloric acid (2×25 ml), water (25 ml) and saturated sodium chloride solution (25 ml) The solution
  4. dry with materialwas dried (MgSO4) and volatile material
  5. customwas removed by evaporation
  6. customThe residue was recrystallised from isohexane

Sources & evidence

ORD record
ord-4370f139e83d4208890741594ad291fb
Source dataset
uspto-grants-1997_09
Patent number
US05668137

Reaction notes

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