2,2',2'',2'''-[(2,3-Dihydroxy-1,4-phenylene)bis(methylenenitrilo)]tetraacetic acid → HCID 86654530, compound

HRID 408888Notes

Reaction equation

[OH:1][C:2]1[C:7]([OH:8])=[C:6]([CH2:9][N:10]([CH2:15][C:16]([OH:18])=O)[CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]=1[CH2:19][N:20]([CH2:25][C:26]([OH:28])=O)[CH2:21][C:22]([OH:24])=[O:23]>N1C=CC=CC=1>[C:2]([O:1][C:2]1[C:3]([CH2:19][N:20]2[CH2:25][C:26](=[O:28])[O:23][C:22](=[O:24])[CH2:21]2)=[CH:4][CH:5]=[C:6]([CH2:9][N:10]2[CH2:11][C:12](=[O:14])[O:13][C:16](=[O:18])[CH2:15]2)[C:7]=1[O:8][C:7](=[O:8])[CH3:6])(=[O:1])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

2,2′,2″,2′″-(2,3-dihydroxy-1,4-phenylene)bis(methylene)bis(azanetriyl)tetraacetic acid (5 g, 12.5 mmol) was added to acetyl anhydride (10 ml) followed by pyridine (3 ml). The reaction was heated at 70° C. for 5 h. The excess anhydride and pyridine were removed under reduced pressure and the residue was recrystallized in acetyl anhydride. 2.8 g of 3,6-bis((2,6-dioxomorpholino)methyl)-1,2-phenylene diacetate was obtained as white solid (yield: 51%). 3,6-bis((2,6-dioxomorpholino)methyl)-1,2-phenylene diacetate (2.24 g, 10 mmol) was added to the solution of ammonia in methanol (7N, 20 ml). The reaction was stirred at room temperature for 1 hour. After removing methanol, the residue was recrystallized in methanol and acetone. 3.5 g of product was obtained as white solid (yield: 88%).

Workup

customThe excess anhydride and pyridine were removed under reduced pressure
customthe residue was recrystallized in acetyl anhydride

Sources & evidence

ORD record: ord-ad6b9114f7524b8f83203ba332988935
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759364B2

Reaction notes

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