Ammonia → HCID 117651054, compound

HRID 1499972Notes

Reaction equation

HRID 1499972 reaction equation
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]1[S:10][C:9]2[S:11][C:12](=[C:14]3[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][S:15]3)[S:13][C:8]=2[S:7]1.O1CCOCC1.C1COCC1.[NH3:33]>CCOCC>[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]1[S:7][C:8]2[S:13][C:12](=[C:14]3[S:18][C:17]([C:19]([O-:21])=[O:20])=[CH:16][S:15]3)[S:11][C:9]=2[S:10]1.[NH4+:33]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 101575822HCID 101575822, compound

Product 1

HCID 117651054HCID 117651054, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Finely crushed 1 (140 mg, 0.330 mmol) was suspended in a mixed solvent of 1,4-dioxane (31.5 ml), THF (31.5 ml), and Et2O (7.0 ml), and the resultant mixture was irradiated with ultrasonic waves for 15 seconds. The mixture was further charged with 28% aq. NH3 (2.8 ml), and irradiated with ultrasonic waves for 15 seconds. The mixture was vigorously stirred for 14 hours at room temperature, and then left to stand for 1 hour at 5° C. The reaction mixture was then filtered using a membrane filter (H010A047A, Advantec). The filtered product was successively washed with water, THF, and Et2O, and dried under reduced pressure to obtain the target product Compound 1-NH4+ (134 mg, 92%) as a dark red solid.

Workup

  1. customirradiated with ultrasonic waves for 15 seconds
  2. waitleft
  3. waitto stand for 1 hour at 5° C
  4. filtrationThe reaction mixture was then filtered
  5. filtrationfilter (H010A047A, Advantec)
  6. washThe filtered product was successively washed with water, THF, and Et2O
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cdd71f6d08d34a32a14cd84301b36048
Source dataset
uspto-grants-2015_12
Patent number
US09202605B2

Reaction notes

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