Sodium Carbonate → HCID 178479315, compound

HRID 609561Notes

Reaction equation

HRID 609561 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[NH:12])[CH:7]=[CH:8][CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>O.O1CCCC1>[ClH:24].[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[NH:12])[CH:7]=[CH:8][CH:9]=1)=[O:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 691102-Chlorobenzoyl chlorideHCID 178478772HCID 178478772, compound

Product 1

HCID 178479315HCID 178479315, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product of Example 1, step (b), 1.38 g, 0.0050 moles, was dissolved in 20 ml of water. The solution was gradually treated with sodium carbonate, 0.84 g, 0.0100 moles, and cooled to 0° C. A solution of 2-chlorobenzoyl chloride, 0.96 g, 0.0053 moles, in 10 ml of tetrahydrofuran was added. This mixture was allowed to stir over the weekend. The mixture was then diluted with water to 100 ml and washed with 20 ml of chloroform. The mixture was made basic with 50% sodium hydroxide and extracted with 20 ml of chloroform (twice). The chloroform was dried with potassium carbonate, filtered and evaporated by vacuum evaporation. The residue was taken up in 20 ml of isopropanol, treated with 1 ml of concentrated hydrochloric acid, and then diluted to 250 ml with ether. The solid that precipitated was collected by filtration and washed with 10 ml of ether (twice). The solid was then recrystallized with methanol and ether and dried in the vacuum oven to provide N-(3-(((2-chlorophenyl)carbonyl)amino)phenyl)-1-pyrrolidinecarboximidamide monohydrochloride. Yield: 1.1 g, m.p. 145° C. (dec)

Workup

  1. washwashed with 20 ml of chloroform
  2. extractionextracted with 20 ml of chloroform (twice)
  3. dry with materialThe chloroform was dried with potassium carbonate
  4. filtrationfiltered
  5. customevaporated by vacuum evaporation
  6. additiontreated with 1 ml of concentrated hydrochloric acid
  7. additiondiluted to 250 ml with ether
  8. customThe solid that precipitated
  9. filtrationwas collected by filtration
  10. washwashed with 10 ml of ether (twice)
  11. customThe solid was then recrystallized with methanol and ether
  12. customdried in the vacuum oven

Sources & evidence

ORD record
ord-a707990392e9443abfe5927934d064db
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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