tert-Butyl methyl ether → HCID 21195016, compound

HRID 1291930Notes

Reaction equation

HRID 1291930 reaction equation
Cl.Cl.Cl.Cl.C(NN=C(NCCCC(C)CNC(=NNC(=N)N)[NH:40][C:41]1[CH:46]=[C:45]([C:47](=[O:49])[CH3:48])[CH:44]=[C:43]([C:50](=[O:52])[CH3:51])[CH:42]=1)NC1C=C(C(=NNC(=N)N)C)C=C(C(=NNC(=N)N)C)C=1)(=N)N.[C:59]([C:62]1[CH:63]=[C:64]([CH:66]=[C:67]([C:69](=[O:71])[CH3:70])[CH:68]=1)[NH2:65])(=[O:61])[CH3:60].[CH3:72][CH:73]([CH2:78][CH2:79][CH2:80][N:81]=[C:82]=[O:83])[CH2:74][N:75]=[C:76]=[O:77].COC(C)(C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:59]([C:62]1[CH:63]=[C:64]([NH:65][C:76]([NH:75][CH2:74][CH:73]([CH3:72])[CH2:78][CH2:79][CH2:80][NH:81][C:82]([NH:40][C:41]2[CH:42]=[C:43]([C:50](=[O:52])[CH3:51])[CH:44]=[C:45]([C:47](=[O:49])[CH3:48])[CH:46]=2)=[O:83])=[O:77])[CH:66]=[C:67]([C:69](=[O:71])[CH3:70])[CH:68]=1)(=[O:61])[CH3:60]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 463010Cni H1894HCID 33434841,5-Diisocyanato-2-methylpentaneHCID 178466959HCID 178466959, compound

Product 1

HCID 21195016HCID 21195016, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound 42, FIG. 7J.42: A suspension of 3,5-diacetylaniline (0.354 g) in methylene chloride (7 mL) containing 4-dimethylaminopyridine (5 mg) was treated with 2-methyl-1,5-pentanediyl diisocyanate (0.18 mL). After heating at reflux for 2 hr, the mixture was cooled. An aliquot was treated with t-butyl methyl ether to give seed crystals which were added to the reaction mixture. After stirring several hr, filtration gave 0.120 g of 1,5-bis[([(3,5-diacetylphenyl)amino]carbonyl)amino]-2-methylpentane, mp 128° C. This tetraketone (0.100 g), aminoguanidine hydrochloride (0.115 g), and aminoguanidine dihydrochloride (3 mg) were heated in 95% ethanol (2.5 mL) for 18 hr. Cooling and filtration gave 0.16 g of 1,5-bis[([(3,5-diacetylphenyl)amino]carbonyl)amino]-2-methylpentane tetrakis(amidinohydrazone) tetrahydrochloride (Compound 42) as the tetrahydrate, mp 258°-9° C.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hr
  3. temperaturethe mixture was cooled
  4. customto give seed crystals which
  5. additionwere added to the reaction mixture
  6. filtrationfiltration

Sources & evidence

ORD record
ord-df6353252d3d424c8860b1dca47f3629
Source dataset
uspto-grants-1998_05
Patent number
US05753684

Reaction notes

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