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Triethylamine → HCID 86759439, compound

HRID 1581646
Notes
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Reaction equation

HRID 1581646 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:10]=[CH:11][C:12]([O:19][CH3:20])=[C:13]([CH2:15][C:16]([OH:18])=O)[CH:14]=2)[S:3]1.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>CN(C)C=O>[F:21][C:22]([F:30])([F:31])[C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:16](=[O:18])[CH2:15][C:13]2[CH:14]=[C:9]([CH:8]=[C:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])[CH:10]=[CH:11][C:12]=2[O:19][CH3:20])=[CH:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 76257Diethyl cyanophosphonateHCID 72644366HCID 72644366, compound

Product 1

HCID 86759439HCID 86759439, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

2-[5-[(2,4-Dioxothiazolidin-5-ylidene)methyl]-2-methoxyphenyl]-acetic acid (440 mg, 1.50 mmol), 4-(trifluoromethyl)aniline (242 μL, 1.50 mmol), triethylamine (210 μL, 1.51 mmol) and dehydrated N,N-dimethylformamide (5 mL) were mixed, and, under an atmosphere of argon, diethyl cyanophosphate (228 μL, 1.50 mmol) was added under cooling with ice and stirring. After stirring for 1 hour at room temperature, the mixture was allowed to stand for 3 days. The reaction mixture was poured into ice water and the precipitated crystals were collected by filtration. The crystals were washed with ethyl acetate, and then dried to obtain 472 mg (72%) of the title compound as yellow crystals.

Workup

  1. temperatureunder cooling with ice
  2. stirringAfter stirring for 1 hour at room temperature
  3. filtrationthe precipitated crystals were collected by filtration
  4. washThe crystals were washed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-b5b4a917aebf4709b0459788ad627d2a
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06730687B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes