Ammonium Hydroxide → HCID 11024571, compound

HRID 1195417Notes

Reaction equation

HRID 1195417 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]2[O:23][CH:22]2[C:24]([O-:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[NH4+:28]>CC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C@@H:21]2[O:23][C@H:22]2[C:24]([NH2:28])=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21470355HCID 21470355, compound

Product 1

HCID 11024571HCID 11024571, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The ester of Example 5c (2R-trans)-(2-napththalenyl) 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate (462 g, 1 mol) was dissolved in acetone (5 L) and ammonium hydroxide (1 L). After stirring briefly at room temperature the reaction mixture was heated to reflux for 20 minutes, recooled to room temperature and concentrated to 1/3 of the original volume on the rotary evaporator. The solution was diluted with toluene (10 L) and washed with 10% aq. NaOH (3×5 L), water (1×5 L) and brine (1×5 L). The toluene solution was further evaporated to a volume of 2.5 L and n-hexane (7.5 L) was added. Upon cooling in the refrigerator (~12 h), the solid was collected and dried to yield the titled oxiranecarboxamide (302 g, 86%). Mp 81°-82° C.; [α]D +13.2° (c 1, CH2Cl2, 25° C.), [α] 546 +16.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 minutes
  3. customrecooled to room temperature
  4. concentrationconcentrated to 1/3 of the original volume on the rotary evaporator
  5. additionThe solution was diluted with toluene (10 L)
  6. washwashed with 10% aq. NaOH (3×5 L), water (1×5 L) and brine (1×5 L)
  7. customThe toluene solution was further evaporated to a volume of 2.5 L and n-hexane (7.5 L)
  8. additionwas added
  9. temperatureUpon cooling in the refrigerator (~12 h)
  10. customthe solid was collected
  11. customdried

Sources & evidence

ORD record
ord-ccc4c71807734a988df3fffc88df8343
Source dataset
uspto-grants-1992_05
Patent number
US05110959

Reaction notes

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