Ammonia → HCID 19826349, compound

HRID 1086607Notes

Reaction equation

HRID 1086607 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[C:3]=1[NH2:12].Br[C:14]1[S:15][CH:16]=[CH:17]N=1.N>O>[CH3:11][C:9]1[CH:8]=[C:4]2[C:3](=[C:2]([CH3:1])[CH:10]=1)[N:12]=[C:14]1[S:15][CH:16]=[CH:17][N:7]1[C:5]2=[O:6]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 764302-BromothiazoleHCID 122648222-Amino-3,5-dimethylbenzamide

Product 1

HCID 19826349HCID 19826349, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 13.1 g of 3,5-dimethylanthranilamide and 13.1 g of 2-bromothiazole was heated for 30 minutes at 155° C. and stirred for 12 hours. After the mixture had cooled to 25° C., the pH was adjusted to 9 by adding water and 25% strength ammonia solution, while stirring, and the resulting solution was stirred for 10 minutes. The solution was then suction filtered and the filtrate was washed with methanol and dried, 10.5 g of the above compound was obtained; m.p. 190°-192° C. The methanol filtrate was concentrated, taken up in ethyl acetate and chromatographed over aluminum oxide. After concentration a further 4.4 g of the above compound were obtained; total yield: 81%.

Workup

  1. temperatureAfter the mixture had cooled to 25° C.
  2. stirringwhile stirring
  3. stirringthe resulting solution was stirred for 10 minutes
  4. filtrationsuction filtered
  5. washthe filtrate was washed with methanol
  6. customdried

Sources & evidence

ORD record
ord-23b55c8bbded4ef887a59738a90a836e
Source dataset
uspto-grants-1991_07
Patent number
US05030727

Reaction notes

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