Ammonia → HCID 18509237, compound

HRID 1356637Notes

Reaction equation

HRID 1356637 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7](O)=[O:8])[C:5]([N:11]([CH3:22])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:4][CH:3]=1.[N:23]1C=CC=CC=1.ClC(OC(C)C)=O.N>C(#N)C.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:11]([CH3:22])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[C:6]([C:7](=[O:8])[NH2:23])[CH:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 18509230HCID 18509230, compound

Product 1

HCID 18509237HCID 18509237, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

5-Chloro-N-methyl-N-(p-toluenesulfonyl)anthranilic acid (5.00 g (14.7 mmol)) and pyridine (1.33 ml (16.4 mmol)) were dissolved in 70.0 ml of acetonitrile. To this, under cooling with ice and with stirring, isopropyl chloroformate (2.00 g (16.3 mmol)) was added dropwise. After 30 minutes' stirring under ice-cooling, ammonia gas (ca. 1.25 g (73.4 mmol)) was bubbled into the reaction mixture. The resulting mixture was stirred under cooling with ice for 30 minutes and at room temperature for 20 hours, and then concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water, dilute sodium hydroxide solution and water, successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to give crude crystals. Diethyl ether was added to these crystals, followed by filtration and washing, to give 1.70 g (34%) of the title compound.

Workup

  1. temperatureTo this, under cooling with ice
  2. stirringAfter 30 minutes' stirring under ice-
  3. temperaturecooling
  4. stirringThe resulting mixture was stirred
  5. concentrationconcentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with water, dilute sodium hydroxide solution and water
  9. dry with materialsuccessively, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give crude crystals
  12. filtrationfollowed by filtration
  13. washwashing

Sources & evidence

ORD record
ord-57c5f442b2a64a59aa059c03cdfd3f79
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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