Diethyl Ether → HCID 67943868, compound

HRID 1199336Notes

Reaction equation

HRID 1199336 reaction equation
[I-:1].[CH2:2]([N+:4]1[C:8]2[CH:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:12][C:7]=2[O:6][C:5]=1[CH3:18])[CH3:3].[C:19]1([N:25](C2C=CC=CC=2)[CH:26]=N)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>CC(C)=O>[I-:1].[NH:25]([CH:26]=[CH:18][C:5]1[O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:9][C:8]=2[N+:4]=1[CH2:2][CH3:3])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 78296Methanimidamide, N,N-diphenyl-HCID 23042805HCID 23042805, compound

Product 1

HCID 67943868HCID 67943868, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Intermediate E (1.0 g) and diphenylformamidine (2.2 g) were combined in a flask and heated over a hot air gun with manual stirring until a yellow-orange color formed. The reaction was then heated for 1 minute at full heat until it became totally liquid. On cooling to room temperature, the reaction mixture solidified. This solid was dissolved in 20 ml hot acetone, poured into 100 ml diethyl ether with stirring, and stirred for 1 hour. The solid was then filtered out and washed with diethyl ether to give 1.2 g of 2-(2-anilinovinyl)-3-ethyl-5-methylsulfonamidobenzoxazolium iodide (Intermediate F).

Workup

  1. temperatureheated over a hot air gun
  2. customformed
  3. temperatureThe reaction was then heated for 1 minute
  4. temperatureat full heat until it
  5. stirringwith stirring
  6. stirringstirred for 1 hour
  7. filtrationThe solid was then filtered out
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b185a4c5ccac4374bde6325546b79835
Source dataset
uspto-grants-1990_02
Patent number
US04900652

Reaction notes

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