Dimethylformamide → 2-Nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate

HRID 1074153Notes

Reaction equation

HRID 1074153 reaction equation
[CH:1]1([C:7]2([C:13](Cl)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:16][CH:17]1[CH2:22][NH:21][C:20](=[N:23][N+:24]([O-:26])=[O:25])[NH:19][CH2:18]1.CN(C=O)C>C(#N)C>[CH:1]1([C:7]2([C:13]([O:16][CH:17]3[CH2:18][NH:19][C:20](=[N:23][N+:24]([O-:26])=[O:25])[NH:21][CH2:22]3)=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 221559231-Cyclohexylcyclohexane-1-carbonyl chlorideHCID 1354218735-Hydroxy-2-nitroiminohexahydropirimidine

Product 1

HCID 1356181062-Nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylateYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-cyclohexylcyclohexane-1-carbonyl chloride (2.1 g) in acetonitrile (30 ml), 5-hydroxy-2-nitroiminohexahydropirimidine (1.28 g) was added portionwise. The mixture was stirred at room temperature overnight, then DMF (10 ml) was added and the mixture was heated to 50° C. for 24 hours. The reaction was quenched with water. The precipitate was collected, dried and triturated with diethyl ether to afford 0.93 g of 2-nitroiminohexahydropyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate.

Workup

  1. temperaturethe mixture was heated to 50° C. for 24 hours
  2. customThe reaction was quenched with water
  3. customThe precipitate was collected
  4. customdried
  5. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-0643903a040e48b0bd1b612fa1ac4aab
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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