Hydrochloric Acid → HCID 10978024, compound

HRID 1532426Notes

Reaction equation

HRID 1532426 reaction equation
C([CH:4](CCC)[CH2:5][NH:6][C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)(O)=O.[OH-:20].[Na+].[O-:22][C:23]#[N:24].[Na+].Cl.[OH2:27]>>[Cl:16][C:14]1[CH:15]=[C:7]2[C:8]([C:9](=[O:11])[NH:24][C:23](=[O:22])[N:6]2[CH2:5][C:4]([OH:27])=[O:20])=[CH:12][CH:13]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium Hydroxide2×HCID 517096Sodium CyanateHCID 21251990HCID 21251990, compound

Product 1

HCID 10978024HCID 10978024, compoundYield 80.3%

Procedure

To a suspension of 2-carboxymethylamino-4-benzoic acid (VIII) (7 g) in water (60 ml) was added 25% aqueous sodium hydroxide (5.95 g) to adjust to pH 5.7. A solution of sodium cyanate (4.58 g) in water (37 ml) was added dropwise to the resulting solution at 35° C. over 2.5 hours. During this dropwise addition, the pH of the reaction solution was adjusted to 5.7 with concentrated hydrochloric acid. After the completion of dropping, the reaction was further continued at the same temperature and pH for one hour. Then, 25% aqueous sodium hydroxide (10.8 g) was added in the solution and the resulting solution was reacted at 60° C. for 10 minutes, hereinafter, was treated in the same manner as in Example 20 to give 6.0 g of the desired compound (yield, 80.3%).

Workup

  1. additionDuring this dropwise addition
  2. customthe resulting solution was reacted at 60° C. for 10 minutes
  3. additionhereinafter, was treated in the same manner as in Example 20

Sources & evidence

ORD record
ord-d18e3fbd42d34b42892681ad1a752721
Source dataset
uspto-grants-2001_03
Patent number
US06201121B1

Reaction notes

Loading…