Trityl chloride → HCID 22961978, compound

HRID 397808Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:22]1([C:28](Cl)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:1]([O:3][C:4]([CH:6]1[C:14]2[N:13]=[CH:12][N:11]([C:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4,5,6,7-tetrahydro-1H-benzimidazole-4-carboxylic acid ethyl ester (18.9 g, 97 mmol, J. Am. Chem. Soc., 1996, 98, 984) in acetonitrile (250 ml) were added triethylamine (27 ml, 194 mmol) and a solution of triphenylmethyl chloride (40.6 g, 146 mmol) in acetonitrile (500 ml). The resulting mixture was stirred at 20° C. overnight. The mixture was concentrated under reduced pressure and the residue was re-dissolved in ethyl acetate, washed with water (2×) and brine (1×), and concentrated under reduced pressure. The residue was recrystallised from ethyl acetate/heptane, to yield 20.8 g (49%) of 1-triphenylmethyl-4,5,6,7-tetrahydro-1H-benzimidazole-4-carboxylic acid ethyl ester as colourless solid. From the mother liquor more product (10.3 g, 24%) was isolated by column chromatography (silica gel, gradient elution with heptane/ethyl acetate 9:1 to 1:1).

Workup

concentrationThe mixture was concentrated under reduced pressure
dissolutionthe residue was re-dissolved in ethyl acetate
washwashed with water (2×) and brine (1×)
concentrationconcentrated under reduced pressure
customThe residue was recrystallised from ethyl acetate/heptane

Sources & evidence

ORD record: ord-97af126c86a340c09fc11274e69f7134
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610721B2

Reaction notes

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