Sodium hydride → HCID 53751272, compound

HRID 845388Notes

Reaction equation

HRID 845388 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH2:10][NH:9][C:8]2=[CH:13][N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[H-].[Na+].[C:21](OC=O)(=[O:23])C>CN(C)C=O>[CH:21]([N:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][CH:17]=2)[C:8]1=[CH:13][N+:14]([O-:16])=[O:15])=[O:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75269Acetic-formic anhydrideHCID 678444081-[(4-Chlorophenyl)methyl]-2-(nitromethylidene)hexahydropyrimidine

Product 1

HCID 53751272HCID 53751272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-Chlorobenzyl)-2-nitromethylene-hexahydropyrimidine (3 g) was added to a stirred suspension of sodium hydride (0.54 g) in dry dimethylformamide (150 ml) at room temperature under nitrogen and the stirring was continued overnight. Formic acetic anhydride (100% excess) was then added dropwise to the stirred suspension at 0°. The reaction mixture was then stirred for 1 hour. It was then poured onto water and extracted with dichloromethane (2×200 ml). The combined organic layers were dried (sodium sulphate) and the solvent removed in vacuo, to leave a solid. The solid was triturated with chloroform (5 ml) and was then filtered off, washed with chloroform (5 ml) and dried to afford the title compound (1.2 g), m.pt. 131°-133° C.

Workup

  1. additionIt was then poured onto water
  2. extractionextracted with dichloromethane (2×200 ml)
  3. dry with materialThe combined organic layers were dried (sodium sulphate)
  4. customthe solvent removed in vacuo
  5. customto leave a solid
  6. customThe solid was triturated with chloroform (5 ml)
  7. filtrationwas then filtered off
  8. washwashed with chloroform (5 ml)
  9. customdried

Sources & evidence

ORD record
ord-952c15934386463ca715b51f4663c9b1
Source dataset
uspto-grants-1988_07
Patent number
US04758570

Reaction notes

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