Toluene → Squaric Acid Distearylperimidine

HRID 718476

Reaction equation

HRID 718476 reaction equation
[C:1]1([OH:8])[C:5](=[O:6])[C:3](=[O:4])[C:2]=1[OH:7].C1(C)C=CC=CC=1.[CH2:16]([C:34]1[CH:45]=[CH:44][C:43]2[C:46]3[C:35]=1[N:36]=[C:37]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[NH:38][C:39]=3[CH:40]=[CH:41][CH:42]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(O)CCC>[C:1]1([OH:8])[C:2](=[O:7])[C:3](=[O:4])[C:5]=1[OH:6].[CH2:16]([C:34]1[CH:45]=[CH:44][C:43]2[C:46]3[C:35]=1[N:36]=[C:37]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[NH:38][C:39]=3[CH:40]=[CH:41][CH:42]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 1140TolueneHCID 17913Squaric acid2×HCID 131734169Distearylperimidine

Product 1

HCID 131734168Squaric Acid DistearylperimidineYield 78%

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 2.0 g squaric acid (MW=114), 50 g toluene and 50 g butanol. The round bottom flask was placed in an 80° C. to 90° C. oil bath. After the squaric acid dissolved, 22.3 g distearylperimidine (MW=635) was added. The reaction progress was monitored by uv-vis spectrum, the results of which are illustrated in FIG. 1. The peak at about 811 nm grew and the peak at 355 decreased. After 3.5 hours the absorbance ratio at 811 nm to 355 nm reached the max 11.62. The reaction mixture was quenched in about 400 ml methanol after 5 hrs of reaction. Sticky solids came out and were filtered and rinsed with more methanol three times. The very sticky solids were dissolved in THF and subsequently dried. The yield was about 78%

Workup

  1. customwas placed in an 80° C. to 90° C.
  2. customthe results of which
  3. customThe reaction mixture was quenched in about 400 ml methanol after 5 hrs of reaction
  4. filtrationwere filtered
  5. washrinsed with more methanol three times
  6. dissolutionThe very sticky solids were dissolved in THF
  7. customsubsequently dried

Sources & evidence

ORD record
ord-3570a66d524e4e678224a4bac3413148
Source dataset
uspto-grants-2015_11
Patent number
US09193869B2

Linked notes

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