Sodium hydride → 1-(6-Chloro-3-pyridylmethyl)-1-formyl-3,3-dimethyl-2-nitroguanidine

HRID 1087108Notes

Reaction equation

HRID 1087108 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([N:15]([CH3:17])[CH3:16])=[N:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].[CH:20](OC(=O)C)=[O:21]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:20]=[O:21])[C:10]([N:15]([CH3:17])[CH3:16])=[N:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75269Acetic-formic anhydrideHCID 1362181971-(6-Chloro-3-pyridylmethyl)3,3-dimethyl-2-nitroguanidine

Product 1

HCID 545004451-(6-Chloro-3-pyridylmethyl)-1-formyl-3,3-dimethyl-2-nitroguanidineYield 34.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.26g of 1-(6-chloro-3-pyridylmethyl)-3,3-dimethyl-2-nitroguanidine (Compound No. 6) and 3ml of dry THF was added 0.08g of 60% sodium hydride (in mineral oil) in a water bath of 20° C., followed by stirring for 30 minutes. A solution of 0.26g of acetic formic anhydride in 0.5ml of THF was added to the reaction mixture in one minute, and then stirred for 12 hours after the bath was removed. After adding 0.5ml of acetic: acid, the reaction mixture was concentrated. The residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (30:1)] to obtain 0.10g of 1-(6-chloro-3-pyridylmethyl)-1-formyl-3, 3-dimethyl-2-nitroguanidine (Compound No. 22) as a syrup.

Workup

  1. stirringstirred for 12 hours after the bath
  2. customwas removed
  3. additionAfter adding 0.5ml of acetic
  4. concentrationacid, the reaction mixture was concentrated
  5. customThe residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (30:1)]

Sources & evidence

ORD record
ord-32e0791080f54e0d96974d93f52dddaf
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Reaction notes

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