1,3-Propanedithiol → [4-(3-Mercaptopropylsulfanyl)-3-methylpyridin-2-yl]methanol

HRID 1637614

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([SH:11])[CH2:8][CH2:9][SH:10].Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]>O>[SH:10][CH2:9][CH2:8][CH2:7][S:11][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][OH:21])[C:15]=1[CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of potassium carbonate (691 g, 5 mol) in 1.5 l of water is treated with 1,3-propanedithiol (432.8 g, 4 mol) under a nitrogen atmosphere and heated to 80° C. A solution of (4-chloro-3-methylpyridin-2-yl)methanol hydrochloride (194.1 g, 1 mol) in 400 ml of water is then added dropwise at this temperature with vigorous stirring during the course of about 2 h. The mixture is additionally stirred at 80 to 85° C. for 18 h and then cooled to room temperature. After separating off the aqueous phase, the organic phase is treated with toluene (1.5 l) and washed with water (2×1 l). The organic phase is then extracted with 2M hydrochloric acid (2 l). The hydrochloric acid phase is concentrated and the residue is recrystallized from isopropanol. 159 g (60%) of the title compound are isolated. The crude product is employed without further purification for the synthesis of the compound of Example 1.

Workup

stirringThe mixture is additionally stirred at 80 to 85° C. for 18 h
temperaturecooled to room temperature
customAfter separating off the aqueous phase
additionthe organic phase is treated with toluene (1.5 l)
washwashed with water (2×1 l)
extractionThe organic phase is then extracted with 2M hydrochloric acid (2 l)
concentrationThe hydrochloric acid phase is concentrated
customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record: ord-ec4eb38a64b045939f884a1987e9437b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043242

Linked notes

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