Dimethylformamide → HCID 178470492, compound

HRID 1053629Notes

Reaction equation

HRID 1053629 reaction equation
O=P(Cl)(Cl)Cl.[C:6]([NH:9][N:10]=[C:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=O)N.[OH-].[Na+].CN([CH:23]=[O:24])C>>[CH:23]([C:17]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][NH:9][CH:6]=1)=[O:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 247973Ethyl 2-(carbamoylhydrazono)propanoate

Product 1

HCID 178470492HCID 178470492, compoundYield 30%

Conditions

Temperature
0 °C

Procedure

POCl3 (532 mL) was added drop-wise to DMF (1 L) at 0° C. over 1 h. The solution was stirred at 0° C. for 1 h, and then product (1-B) (200 g, 0.9 mol) was added in small portions while the reaction temperature was maintained below 5° C. After the addition, the reaction was heated to 80° C. and stirred for another 4 hours. The solution was poured into ice water, and the pH was adjusted to 7 with 2 M NaOH, while maintaining the temperature below 5° C. After standing overnight, the solid was filtered, washed with H2O, and dried in vacuo to give crude product (2-B) (46 g, 30%, for two steps) as a yellow solid. 1H NMR (300 MHz, d-DMSO): δ 14.14 (br, 1H), 10.27 (s, 1H), 8.52 (br, 1H), 4.38 (q, 2H), 1.35 (t, 3H). LC-MS (M+H)+=169.

Workup

  1. temperaturewas maintained below 5° C
  2. additionAfter the addition
  3. temperaturethe reaction was heated to 80° C.
  4. stirringstirred for another 4 hours
  5. temperaturewhile maintaining the temperature below 5° C
  6. waitAfter standing overnight
  7. filtrationthe solid was filtered
  8. washwashed with H2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-661eaac892db417db4a89a81da5039d4
Source dataset
uspto-grants-2016_07
Patent number
US09394256B2

Reaction notes

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