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

HRID 1584256Notes

Reaction equation

HRID 1584256 reaction equation
[N:1]([CH2:4][C:5]1[N:9]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[N:7][C:6]=1[CH3:29])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[C:10]([N:9]1[C:5]([CH2:4][NH2:1])=[C:6]([CH3:29])[N:7]=[CH:8]1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 212245615-Azidomethyl-4-methyl-1-tritylimidazole

Product 1

HCID 21224562(4-methyl-1-trityl-1H-imidazol-5-yl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-azidomethyl-4-methyl-1-tritylimidazole (3.0 g, 7.9 mmol) in THF (70 ml) was added triphenylphosphine (5.18 g, 19.8 mmol). The resulting solution was refluxed for 1.5 h then water (5 ml) was added. Refluxing was continued for an additional 24 hours. After cooling to room temperature, the solvents were removed in vacuo and the crude reaction mixture was purified by chromatography on silica gel (19:1 chloroform/10% NH4OH in methanol) to give of the title compound. 1H NMR (CDCl3) d 1.40 (s, 3 H), 1.70 (br s, 2 H), 3.70 (s, 2 H), 7.10-7.35 (m, 16 H).

Workup

  1. temperatureThe resulting solution was refluxed for 1.5 h
  2. temperatureRefluxing
  3. customthe solvents were removed in vacuo
  4. customthe crude reaction mixture
  5. customwas purified by chromatography on silica gel (19:1 chloroform/10% NH4OH in methanol)

Sources & evidence

ORD record
ord-817207cb1e5049dc8bf2f2b7cb66ed01
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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