Squaric acid → Squaric Acid Hydroxymethylperimidine

HRID 718477

Reaction equation

HRID 718477 reaction equation
[C:1]1([OH:8])[C:5](=[O:6])[C:3](=[O:4])[C:2]=1[OH:7].OC[CH2:11][C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:24]=2[C:22]([N:23]=1)=[CH:21][CH:20]=[CH:19]3>C(O)CCC>[C:1]1([OH:8])[C:2](=[O:7])[C:3](=[O:4])[C:5]=1[OH:6].[OH:4][CH2:11][C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:24]=2[C:22]([N:23]=1)=[CH:21][CH:20]=[CH:19]3

Participants

4

Reactant 2

HCID 17913Squaric acid2×HCID 117903368Hydroxyethyl perimidine

Product 1

HCID 131734170Squaric Acid Hydroxymethylperimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a 100 ml round bottom flask equipped with Teflon coated stir magnetic and a condenser was charged 1 g squaric acid (MW=114) and 45 g butanol. The round bottom flask was placed in an 80° C. oil bath. After the squaric acid dissolved, 4.0 g of the hydroxyethyl perimidine was added, as shown in the reaction below. The reaction progress was monitored by uv-vis spectrum. The peak at about 812 nm grew and peak at 354 decreased. The reaction was stopped when the 812 nm peak was considered maximized.

Workup

  1. customwas placed in an 80° C.
  2. customas shown in the reaction below

Sources & evidence

ORD record
ord-119d6afa16aa4be2ae1f88ddd9f1e80b
Source dataset
uspto-grants-2015_11
Patent number
US09193869B2

Linked notes

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