Ammonia → (4-methyl-1-trityl-1H-imidazol-5-yl)methanamine

HRID 249930Notes

Reaction equation

HRID 249930 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[N:5][C:4]=1[CH3:27].[NH3:28]>>[CH3:27][C:4]1[N:5]=[CH:6][N:7]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:3]=1[CH2:2][NH2:28]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 668733865-(chloromethyl)-4-methyl-1-trityl-1H-imidazole

Product 1

HCID 21224562(4-methyl-1-trityl-1H-imidazol-5-yl)methanamineYield 26.4%

Procedure

A solution of 5-(chloromethyl)-4-methyl-1-trityl-1H-imidazole (1.00 g, 2.68 mmol) in ammonia (7 N in CH3OH, 4 mL, 28 mmol) was heated to 50° C. in a sealed tube for 16 h. The reaction mixture was concentrated under reduced pressure and the crude material purified by column chromatography (silica gel, 100% CH2Cl2 to 50% CH3OH) to provide (4-methyl-1-trityl-1H-imidazol-5-yl)methanamine (250 mg, 26%). 1H NMR consistent.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude material purified by column chromatography (silica gel, 100% CH2Cl2 to 50% CH3OH)

Sources & evidence

ORD record
ord-d6e724c48a1d4879859aa8d4f95db731
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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