Formaldehyde → HCID 57496010, compound

HRID 2071144Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:16]([CH:18]=O)=O.[NH4+:20].[Cl-].[CH2:22]=O.OP(O)(O)=O>CCO>[N:1]1([C:2]2[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=[C:4]([CH:3]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:18]=[CH:16][N:20]=[CH:22]1

Participants

Conditions

Temperature: 90 °C

Procedure

Dimethyl 5-aminoisophthalate (1.00 g, 4.78 mmol, 1 eq) and glyoxal trimer 2H2O (1.004 g, 4.78 mmol, 1 eq) were stirred in 6 ml EtOH overnight. NH4Cl (0.5114 g, 9.56 mmol, 2 eq) was added. After 15 min aqueous formaldehyde (37%, 0.71 ml, 0.78 g, 9.56 mmol, 2 eq) was added and the mixture was heated to reflux at 90° C. After 1 h the reaction was cooled to room temperature. After the dropwise addition of H3PO4 (85%, 0.65 ml, 1.1 g, 9.56 mmol, 2 eq) the reaction was heated to reflux at 95° C. After 6 h the reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was stirred in CHCl3 and the mixture was filtered through cotton to remove any insoluble material. Purification via flash chromatography yielded 0.7329 g (2.82 mmol, 59% yield) of dimethyl 5-(1H-imidazol-1-yl)isophthalate.

Workup

temperaturethe mixture was heated
temperatureAfter 1 h the reaction was cooled to room temperature
temperaturewas heated
temperatureto reflux at 95° C
temperatureAfter 6 h the reaction was cooled to room temperature
customthe solvent was removed in vacuo
filtrationthe mixture was filtered through cotton
customto remove any insoluble material
customPurification via flash chromatography

Sources & evidence

ORD record: ord-b99985f5833143ea8d66343a593192ab
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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