Ammonia → HCID 57096431, compound

HRID 569306Notes

Reaction equation

HRID 569306 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18](O)=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH2:22][O:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:30])[CH:5]=1.[NH3:31]>O1CCCC1>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([O:16][CH2:17][C:18]([NH2:31])=[O:19])[CH:12]=[C:11]2[C:3]=1[C:4]1[C:9]([CH2:21][CH2:22][O:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])([CH2:10]2)[CH2:8][CH2:7][C:6](=[O:30])[CH:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86742044HCID 86742044, compound

Product 1

HCID 57096431HCID 57096431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

{[(5,6-Dichloro-3-oxo-2,3,9,9a-tetrahydro-9a-(2-trifluoroacetoxyethyl)-1H-fluoren-7-yl]oxy}acetic acid (4.67 g, 10 mMole) is dissolved in tetrahydrofuran (30 ml) and 1,1-carbonyldiimidazole (1.78 g, 11 mMole) and the mixture stirred at ambient temperature for 30 minutes. The solution is saturated with ammonia gas and then stirred at ambient temperature for 24 hours and at 50° C. for 16 hours. Evaporation of the solvent and recrystallization from nitromethane yields [(5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-9a-(2-trifluoroacetoxyethyl)-1H-fluoren-7-yl)oxy]acetamide.

Workup

  1. customEvaporation of the solvent and recrystallization from nitromethane

Sources & evidence

ORD record
ord-388b231a32764aa5ac434df822384f4f
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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