Carbon Disulfide → 5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,3,4-thiadiazole-2(3H)-thione

HRID 1492987Notes

Reaction equation

HRID 1492987 reaction equation
[C:1](=[S:3])=[S:2].[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([C:25]([NH:27][NH2:28])=N)[CH:11]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])([CH3:7])[CH3:6]>C(O)C.C(OC(C)C)(C)C>[CH3:7][C:5]([C:8]1[CH:9]=[C:10]([C:25]2[S:2][C:1](=[S:3])[NH:28][N:27]=2)[CH:11]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]=1[O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])([CH3:4])[CH3:6]

Participants

5

Reactant 2

HCID 6348Carbon DisulfideHCID 178496297HCID 178496297, compound

Product 1

HCID 103415325-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,3,4-thiadiazole-2(3H)-thioneYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 7914Diisopropyl EtherSolvent

Procedure

Carbon disulfide (1.6 g, 0.021 mole) is added dropwise to a stirred 0° C. solution of 3,5-bis(1,1- dimethylethyl)-4-[(2-methoxyethoxy)methoxy]benzene carboximidic acid hydrazide (3.0 g, 0.085 mole) in absolute ethanol (36 ml). The mixture is allowed to warm to room temperature and stir three hours. The mixture is stripped of volatiles under reduced pressure and the residue is dissolved in isopropyl ether and the solvent removed under reduced pressure. The resulting solid is recrystallized from isopropyl ether/hexane to give 2.8 g of 5-[3,5-bis(1,1-dimethylethyl)-4-[(2-methoxyethoxy)methoxy]phenyl]-1,3,4-thiadiazole-2(3H)-thione (3.5 g theor., 80%); mp 134°-135° C.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe resulting solid is recrystallized from isopropyl ether/hexane

Sources & evidence

ORD record
ord-37296009599645a294d5fcb83b271c96
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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