Ethanol → HCID 178481281, compound

HRID 2286430Notes

Reaction equation

HRID 2286430 reaction equation
[Na].[CH2:2]([OH:4])[CH3:3].[C:5]([CH2:7][C:8]([NH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17]OCC1)=O)#[N:6].[Cl:19][C:20]1[CH:32]=[C:24]2[C:25](O[C:28](=O)[N:29](C)[C:23]2=[CH:22][CH:21]=1)=[O:26].[OH2:33]>>[Cl:19][C:20]1[CH:32]=[C:24]2[C:23](=[CH:22][CH:21]=1)[N:29]([CH3:28])[C:5](=[NH:6])[C:7]([C:8]([NH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:4][CH2:2][CH2:3]1)=[O:33])=[C:25]2[OH:26]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 267242H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro-1-methyl-HCID 24048752-Cyano-N-[2-(morpholin-4-yl)ethyl]acetamideHCID 5360545Sodium

Product 1

HCID 178481281HCID 178481281, compound

Procedure

To a solution of 0.92 g. (0.04 g. atoms) of sodium dissolved in 50 ml. of absolute ethanol was added 7.88 g. (0.04 mole) of 2-cyano-N-(2- morpholinoethyl)acetamide. The solvent was removed in a rotary evaporator in vacuo. Dimethyl formamide (50 ml.) was added to the residue followed by 8.46 g. (0.04 mole) of 5-chloro-N-methylisatoic anhydride. The reaction mixture was heated under reflux for 4 hours, cooled in ice and then poured into 1-liter of water. The resulting precipitate was collected and recrystallized from ethanol giving 5.6 g. of product, m.p. 211°-213° C.

Workup

  1. customThe solvent was removed in a rotary evaporator in vacuo
  2. additionDimethyl formamide (50 ml.) was added to the residue
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 4 hours
  5. temperaturecooled in ice
  6. customThe resulting precipitate was collected
  7. customrecrystallized from ethanol giving 5.6 g

Sources & evidence

ORD record
ord-4128bd300dc64410bcb9c64771fc7fbd
Source dataset
uspto-grants-1981_05
Patent number
US04266050

Reaction notes

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