Benzyl chloroformate → HCID 53824026, compound

HRID 1168334Notes

Reaction equation

HRID 1168334 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:12]([NH:22][CH3:23])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>ClCCl.C(N(C(C)C)C(C)C)C>[CH2:28]([O:27][C:25](=[O:26])[N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:12]([NH:22][CH3:23])=[CH:11][N:10]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 23502774HCID 23502774, compound

Product 1

HCID 53824026HCID 53824026, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 2.03 g (6.7 mmol) N2-benzyl-N5-methyl-4-o-tolyl-pyridine-2,5-diamine in 100 ml dichloromethane and 40 ml N-ethyldiisopropylamine a solution of 2.1 ml (14.09 mmol) benzyl chloroformate in 50 ml dichloromethane was added dropwise at 0° C. After stirring for 2 h at room temperature the reaction mixture was washed with water (2×50 ml), brine (50 ml), dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 2.36 g (80%) of the title compound as light brown crystals. M.p. 110-112° C. MS m/e (%): 438 (M+H+, 100).

Workup

  1. washwas washed with water (2×50 ml), brine (50 ml)
  2. dry with materialdried (magnesium sulfate)
  3. customevaporated

Sources & evidence

ORD record
ord-603ead97ba3546409efa0d35c0a44c74
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

Loading…