Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl ester → HCID 11329229, compound

HRID 1072477Notes

Reaction equation

HRID 1072477 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]([CH3:17])([CH3:16])[C:14]#[N:15])=[C:8]([Cl:18])[CH:7]=1.C([O-])(=O)C.[Na+].[CH2:24]([O:26][C:27](=[O:40])[NH:28][C:29](=[O:39])[CH2:30][C:31]([NH:33][C:34](=[O:38])[O:35][CH2:36][CH3:37])=[O:32])[CH3:25]>O.C(O)(=O)C.Cl>[Cl:18][C:8]1[CH:7]=[C:6]([NH:5][N:1]=[C:30]([C:31]([NH:33][C:34](=[O:38])[O:35][CH2:36][CH3:37])=[O:32])[C:29]([NH:28][C:27](=[O:40])[O:26][CH2:24][CH3:25])=[O:39])[CH:11]=[C:10]([Cl:12])[C:9]=1[C:13]([C:14]#[N:15])([CH3:16])[CH3:17]

Participants

8

Reactant 4

HCID 154305Carbamic acid, (1,3-dioxo-1,3-propanediyl)bis-, diethyl esterHCID 517045Sodium AcetateHCID 112416692-(4-Amino-2,6-dichloro-phenyl)-2-methyl-propionitrileHCID 23668193Sodium Nitrite

Product 1

HCID 11329229HCID 11329229, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A solution of NaNO2 (0.36 mole) in H2O (50 ml) was added to a solution of intermediate (3) (0.34 mole) in acetic acid (700 ml) and HCl (102 ml), stirred at 10° C. The reaction mixture was stirred for 80 minutes at 10° C. A powdered mixture of sodium acetate (1.02 mole) and diethyl(1,3-dioxo-1,3-propanediyl)biscarbamate (0.374 mole) was added and the reaction mixture was stirred for 40 minutes. The reaction mixture was poured out onto crushed ice. The precipitate was filtered off, washed with water, taken up into CH2Cl2, and the layers were separated. The organic layer was dried, filtered and the solvent evaporated, yielding 138.5 g (84%) of diethyl N,N′-[2-[[3,5-dichloro-4-(1-cyano-1-methylethyl)phenyl]hydrazono]-1,3-dioxo-1,3-propanediyl]dicarbamate (intermediate 4).

Workup

  1. stirringThe reaction mixture was stirred for 80 minutes at 10° C
  2. additionwas added
  3. stirringthe reaction mixture was stirred for 40 minutes
  4. additionThe reaction mixture was poured out
  5. customonto crushed ice
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customthe layers were separated
  9. customThe organic layer was dried
  10. filtrationfiltered
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-e3baf4461cee4dd18dced4638a922300
Source dataset
uspto-grants-2005_06
Patent number
US06911444B2

Reaction notes

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