Methyl Chloride → Hydrazine

HRID 441684Notes

Reaction equation

HRID 441684 reaction equation
[ClH:1].[NH:2]1[CH2:7][CH2:6][CH2:5][N:4]=[C:3]1[NH:8][NH2:9].N1CCCN[C:11]1=[S:16].CCl>C(O)(C)C>[ClH:1].[CH3:11][S:16][C:3]1[NH:2][CH2:7][CH2:6][CH2:5][N:4]=1.[NH2:8][NH2:9]

Participants

6

Reactant 3

HCID 6327Methyl ChlorideHCID 2723785Tetrahydropyrimidine-2-thioneHCID 214170401,4,5,6-Tetrahydropyrimidin-2-ylhydrazine hydrochloride

Product 2

HCID 9321HydrazineHCID 214171322-Methylthio-1,4,5,6-tetrahydropyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
4 °C

Procedure

The preparation of the starting material, 1,4,5,6-tetrahydropyrimidin-2-ylhydrazine hydrochloride, is carried out as follows: 1,4,5,6-tetrahydropyrimidin-2-thione and methyl chloride (excess) are added to isopropanol and the mixture heated in an autoclave at 170°-180° C. for hours. Cooling to 4° C. yields a precipitate of 2-methylthio-1,4,5,6-tetrahydropyrimidine hydrochloride, which upon treatment with hydrazine in boiling ethanol yields the desired intermediate melting at 191°-192° C.

Workup

  1. temperaturethe mixture heated in an autoclave at 170°-180° C. for hours

Sources & evidence

ORD record
ord-ad75af06ea2e46a3a06638c3d8f3065b
Source dataset
uspto-grants-1977_08
Patent number
USRE029358

Reaction notes

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