Imidazo[1,2-a]pyridin-8-ylmethanol → HCID 178423503, compound

HRID 1789201Notes

Reaction equation

HRID 1789201 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[N:5]([CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[SH:12][C:13]1[NH:14][C:15]2[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:16]=2[N:17]=1>>[OH2:1].[N:11]1[CH:10]=[CH:9][N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][S:12][C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=4[N:14]=3)[C:4]=12.[N:11]1[CH:10]=[CH:9][N:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][S:12][C:13]3[NH:17][C:16]4[CH:18]=[CH:19][C:20]([CH3:22])=[CH:21][C:15]=4[N:14]=3)[C:4]=12

Participants

3

Reactant 2

HCID 11029987Imidazo[1,2-a]pyridin-8-ylmethanolHCID 178423448HCID 178423448, compound

Product 1

HCID 178423503HCID 178423503, compound

Procedure

A mixture of 12.2 g (0.1 mole) of 3,4-diaminotoluene, 35 ml of carbon disulfide, and 4.0 g (0.1 mole) of sodium hydroxide was heated at reflux in 350 ml of ethanol. After 2.5 hours the mixture was concentrated in vacuo. The residue was suspended in 200 ml of 4% aqueous hydrochloric acid, collected by filtration, washed sequentially with water and diethyl ether, and air dried to yield 12.2 g of 2-mercapto-5-methylbenzimidazole, as confirmed by the nmr and infrared spectra. The title compound (796 mg) was prepared by the method of Example 6 using 8-hydroxymethylimidazo[1,2-a]pyridine as the hydrochloride salt and using 569 mg (3.5 mmole) of 2-mercapto-5-methylbenzimidazole instead of 2-mercapto-5-methoxybenzimidazole. Structure assignment was supported by elemental analysis.

Sources & evidence

ORD record
ord-e6c84d7e8b524308ae06567cb35cd1c2
Source dataset
uspto-grants-1987_08
Patent number
US04687775

Reaction notes

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