Water → HCID 136341189, compound

HRID 728034Notes

Reaction equation

HRID 728034 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:12][CH3:13])[CH:3]=1.Cl.[N+:15]([NH:18][C:19]([NH:21][CH2:22][CH2:23][NH2:24])=[NH:20])([O-:17])=[O:16].[N:25]12CCCN=C1CCCCC2.O>CN(C)C=O>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([NH:25][NH:20][C:19]([NH:21][CH2:22][CH2:23][NH2:24])=[N:18][N+:15]([O-:17])=[O:16])=[O:8])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 178479350HCID 178479350, compound

Product 1

HCID 136341189HCID 136341189, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4-amino-5-chloro-2-methoxy benzoic acid (0.6 g) and N,N'-carbonyldiimidazole (0.49 g) in anhydrous dimethylformamide (DMF) (15 ml) was stirred at room temperature for 30 minutes, then a solution of N-nitro-N'-aminoethylguanidine hydrochloride (0.55 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in DMF was added. The mixture was stirred for 4 hours at 50° C., then was cooled, poured into water and extracted with methylene chloride. The organic layer was washed with sodium carbonate solution and dried. After cooling, the title compound was collected as a solid, M.p. 226°-227° C. (dec.)

Workup

  1. temperaturewas cooled
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with sodium carbonate solution
  4. customdried
  5. temperatureAfter cooling
  6. customthe title compound was collected as a solid, M.p. 226°-227° C. (dec.)

Sources & evidence

ORD record
ord-b6b77a5c90b74b1284f91f1cb1ac07b4
Source dataset
uspto-grants-1991_09
Patent number
US05047410

Reaction notes

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