Sodium Carbonate → HCID 178452737, compound

HRID 609559Notes

Reaction equation

HRID 609559 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]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[O:26]>O.O1CCCC1>[ClH:24].[CH3:30][CH:29]([CH3:31])[CH2:28][O:27][C:25]([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:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 62365Isobutyl chloroformateHCID 178478772HCID 178478772, compound

Product 1

HCID 178452737HCID 178452737, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

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 O° C. A solution of 0.71 ml of isobutyl chloroformate in 10 ml of tetrahydrofuran was added. After 16 hours the mixture was diluted with water to 100 ml and washed with 20 ml of chloroform. This solution was then made basic with 50% aqueous sodium hydroxide and extracted with 20 ml chloroform (twice). The chloroform layer was dried over potassium carbonate, filtered and the solvent was driven off by vacuum evaporation. The remaining oil was dissolved in 20 ml of isopropanol and 1 ml of concentrated aqueous hydrochloric acid was added. The solution was then made up to 250 ml with ether. Crystals developed and were washed with 10 ml of ether (twice) and dried in a vacuum oven overnight to yield N-(3-(((2-methylpropyloxy)carbonyl)amino)phenyl)-1-pyrrolidinecarboximidamide monohydrochloride. Yield: 1.1 g, m.p. 233-235° C.

Workup

  1. temperaturecooled to O° C
  2. washwashed with 20 ml of chloroform
  3. extractionextracted with 20 ml chloroform (twice)
  4. dry with materialThe chloroform layer was dried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent was driven off by vacuum evaporation
  7. dissolutionThe remaining oil was dissolved in 20 ml of isopropanol
  8. addition1 ml of concentrated aqueous hydrochloric acid was added
  9. washwere washed with 10 ml of ether (twice) and
  10. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-1ec68d0d3ebd4d3e8db5cae357cbe245
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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