Methylamine → HCID 22929709, compound

HRID 1296029Notes

Reaction equation

HRID 1296029 reaction equation
[N:1]([CH2:4][C:5]1[C:13]([Br:14])=[CH:12][C:8]([C:9](O)=[O:10])=[C:7]([O:15][CH2:16][CH3:17])[CH:6]=1)=[N+:2]=[N-:3].[CH3:18][NH2:19]>O1CCCC1.C(N(CC)CC)C.ClC(OCC)=O.C(OCC)(=O)C>[CH3:18][NH:19][C:9](=[O:10])[C:8]1[CH:12]=[C:13]([Br:14])[C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:6][C:7]=1[O:15][CH2:16][CH3:17]

Participants

7

Reactant 2

HCID 6329MethylamineHCID 22929807HCID 22929807, compound

Product 1

HCID 22929709HCID 22929709, compound

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolventHCID 10928Ethyl chloroformateSolvent

Procedure

After dissolving the 4-(azidomethyl)-5-bromo-2-ethoxybenzoic acid (7.67 g) in tetrahydrofuran (100 ml), triethylamine (3.2 ml) and ethyl chloroformate (2.11 ml) were added in that order and the mixture was stirred at room temperature for 30 minutes. Aqueous methylamine (3.2 ml) was added and the mixture was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and washed with water and 1 N hydrochloric acid, and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to yield the title compound (5.328 g) as a white solid.

Workup

  1. additionwere added in that order
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washwashed with water and 1 N hydrochloric acid
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f0c642b6edaa4bfb8861a8f679031930
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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