Aniline → HCID 178448889, compound

HRID 256724Notes

Reaction equation

HRID 256724 reaction equation
OC(C)COC(=O)NC[CH2:8][NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][CH2:15][CH:16]([OH:18])[CH3:17].[N:22]1[C:29](Cl)=[N:28]C(Cl)=[N:25][C:23]=1Cl.C(=O)(O)[O-].[Na+].[CH2:36]([NH2:40])[CH2:37][CH2:38][CH3:39].[NH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(O)CCC.C(OC(=O)C)C>[OH:18][CH:16]([CH3:17])[CH2:15][O:14][C:13]([NH:12][CH2:11][CH2:10][N:9]1[C:8]([NH:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[N:25][C:23]([NH:40][CH2:36][CH2:37][CH2:38][CH3:39])=[N:22][CH:29]1[NH2:28])=[O:19]

Participants

8

Reactant 5

HCID 6115AnilineHCID 7954Cyanuric chloride2×HCID 8007Butylamine2×HCID 516892Sodium BicarbonateHCID 14534466HCID 14534466, compound

Product 1

HCID 178448889HCID 178448889, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suitably equipped 3-necked flask, are added 15.6 g (0.05 m) of bis(2-hydroxypropyl)(imino diethylene)bis carbamate dissolved in 50 g of n-butanol. To this solution are added slowly 9.2 g (0.05 m) of cyanuric chloride dissolved in 75 g of ethylacetate. The reaction mixture is allowed to stir at 0-5° C. and progress of the reaction is monitored by tlc. After all the cyanuric chloride is reacted to the mono substituted product, 8.4 g of sodium bicarbonate and 3.65 g (0.05 m) of n-butylamine are added. The reaction temperature is raised to 35-45° C. and maintained there until most of the n-butylamine has reacted. At this point 4.7 g (0.05 m) aniline are added and the reaction temperature raised to 115° C. after distilling out ethyl acetate. After about 5-6 hours, sodium chloride is filtered off. After removal of n-butanol and reaction work up and above-described product is obtained in high yields. ##STR28## wherein R1 is --N(CH2CH2NHCO2CH(CH3)CH2OH)2 or --N(CH2CH2NHCO2CH2CH(CH3)OH)2 (XV)

Workup

  1. additionare added
  2. temperatureThe reaction temperature is raised to 35-45° C.
  3. customhas reacted
  4. temperaturethe reaction temperature raised to 115° C.
  5. distillationafter distilling out ethyl acetate
  6. filtrationsodium chloride is filtered off
  7. customAfter removal of n-butanol and reaction work up and above-described product
  8. customis obtained in high yields

Sources & evidence

ORD record
ord-3b2ea17d6f1746a79e64b70526230a74
Source dataset
uspto-grants-1993_11
Patent number
US05258514

Reaction notes

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