Butyl iodide → 4-Butoxycarbonyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione

HRID 2420455Notes

Reaction equation

CN(P(N(C)C)(N(C)C)=O)C.[C:12]([C:15]1[C:16](=[S:26])[S:17][S:18][C:19]=1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)([OH:14])=[O:13].[O-]CC.[Na+].[CH2:31](I)[CH2:32][CH2:33][CH3:34]>C(O)C.C(OCC)(=O)C>[CH2:31]([O:13][C:12]([C:15]1[C:16](=[S:26])[S:17][S:18][C:19]=1[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)=[O:14])[CH2:32][CH2:33][CH3:34]

Participants

Conditions

Temperature: 50 °C

Procedure

Anhydrous hexamethylphosphotriamide (5 cc) and 4-carboxy-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (1.28 g) (prepared as described in Example 32) are added to a solution of dry sodium ethoxide (0.34 g) in anhydrous ethanol (5 cc). The suspension obtained is heated to a temperature of about 50° C, the resulting solution is cooled to a temperature of about 20° C and then butyl iodide (1.7 g) is added. The reaction mixture is then maintained at a temperature of about 50° C for 7 hours. An insoluble material is filtered off and the filtrate is evaporated to dryness under reduced pressure (20 mm Hg). The oil obtained is treated with ethyl acetate (2 cc) and the product which crystallises is filtered off and washed with diethyl ether (2 cc). After drying, 4-butoxycarbonyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (0.4 g), melting at 127° C, is obtained.

Workup

customThe suspension obtained
temperaturethe resulting solution is cooled to a temperature of about 20° C
temperatureThe reaction mixture is then maintained at a temperature of about 50° C for 7 hours
filtrationAn insoluble material is filtered off
customthe filtrate is evaporated to dryness under reduced pressure (20 mm Hg)
customThe oil obtained
customthe product which crystallises
filtrationis filtered off
washwashed with diethyl ether (2 cc)
customAfter drying

Sources & evidence

ORD record: ord-6f6e496d8c304f41897d56a7e2c7b716
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04110450

Reaction notes

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