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Ammonia → 2-Hydrazino-5,5-Dimethyl-1,3-Diazacyclohex-2-ene Monohydrochloride

HRID 443974
Notes
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Reaction equation

HRID 443974 reaction equation
[ClH:1].[NH2:2][C:3]1[NH:4][CH2:5][C:6]([CH3:10])([CH3:9])[CH2:7][N:8]=1.[NH3:11]>>[ClH:1].[NH:2]([C:3]1[NH:8][CH2:7][C:6]([CH3:10])([CH3:9])[CH2:5][N:4]=1)[NH2:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 222AmmoniaHCID 234662455,5-Dimethyl-1,4,5,6-tetrahydropyrimidin-2-amine hydrochloride

Product 1

HCID 202453512-Hydrazino-5,5-Dimethyl-1,3-Diazacyclohex-2-ene Monohydrochloride

Procedure

The product (2.60 parts) of Example 1 above, 2-amino-5,5-dimethyl-1,4,5,6-tetrahydropyrimidine hydrochloride, is added to a suitable flask equipped with condenser and magnetic stirring bar, and flushed with argon. There is next added 1.19 parts, 1.5 equivalents, of hydrazine hydrate, and the mixture is stirred until a clear solution is obtained. The flask is then placed in an oil bath preheated to 115° C. Ammonia is evolved almost immediately. The reaction is maintained at 115°-120° C. under a stream of argon for twelve hours. After sitting overnight at room temperature, the flask contains a white, crystalline solid and a small amount of clear, colorless liquid. The liquid is evaporated at room temperature. Resultant yield of 2-hydrazino-5,5-dimethyl-1,4,5,6-tetrahydropyrimidine hydrochloride which is found to be 97% pure is almost quantitative.

Workup

  1. customequipped with condenser and magnetic stirring bar
  2. customflushed with argon
  3. additionThere is next added 1.19 parts, 1.5 equivalents
  4. customis obtained
  5. customThe flask is then placed in an oil bath
  6. custompreheated to 115° C
  7. temperatureThe reaction is maintained at 115°-120° C. under a stream of argon for twelve hours
  8. customThe liquid is evaporated at room temperature

Sources & evidence

ORD record
ord-7b7db32df3db4c6bbf632ff6a11044f2
Source dataset
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04262122

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes