Ethanethiol → 1-[[3-(Ethylthio)-2-pyrazinyl]oxy]-3-[(1-methylethyl)amino]-2-propanol

HRID 1764348Notes

Reaction equation

HRID 1764348 reaction equation
Cl[C:2]1[C:3]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:17]([SH:19])[CH3:18].C[O-].[Na+]>CO>[CH2:17]([S:19][C:2]1[C:3]([O:8][CH2:9][CH:10]([OH:16])[CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[CH:6][N:7]=1)[CH3:18]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10942334Sodium MethoxideHCID 204834181-[(3-Chloropyrazin-2-yl)oxy]-3-[(propan-2-yl)amino]propan-2-ol

Product 1

HCID 204834541-[[3-(Ethylthio)-2-pyrazinyl]oxy]-3-[(1-methylethyl)amino]-2-propanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to the description in Example 8, 7.5 g (0.03 mol) of 3-chloro-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine, 2.8 g (0.045 mol) of ethylmercaptan and 2.4 g (0.045 mol) of sodium methylate in 150 ml of methanol, when refluxed for 30 hours, give the crude base 3-ethylthio-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine, and this is converted, with 1.74 g of fumaric acid, into the fumarate of melting point 158°-160° C. when crystallised from methanol-ether.

Sources & evidence

ORD record
ord-c98619feecea43e4b639201816ccc1e8
Source dataset
uspto-grants-1978_09
Patent number
US04115575

Reaction notes

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