Acetic Anhydride → HCID 178474199, compound

HRID 609558Notes

Reaction equation

HRID 609558 reaction equation
[ClH:1].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+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>O.O1CCCC1>[ClH:1].[CH3:25][C:24]([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 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 178478772HCID 178478772, compound

Product 1

HCID 178474199HCID 178474199, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of the product of 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. Next a solution of 0.5 ml of acetic anhydride in 10 ml of tetrahydrofuran was added. This was stirred overnight under nitrogen. The mixture was diluted with enough water to bring the volume to 100 ml. and washed with 20 ml of chloroform. The aqueous layer 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. The oil was dissolved in ml of isopropanol and treated with 1 ml of concentrated hydrochloric acid. This mix was then diluted to 250 ml with ether. The solids were filtered and washed with 10 ml of ether (twice). The sample was allowed to dry overnight to yield N-(3-((methylcarbonyl)amino)phenyl)-1-pyrrolidinecarboximidamide monohydrochloride. Yield: 350 mg, m.p. 193-196° C.

Workup

  1. washand washed 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
  6. dissolutionThe oil was dissolved in ml of isopropanol
  7. additiontreated with 1 ml of concentrated hydrochloric acid
  8. additionThis mix was then diluted to 250 ml with ether
  9. filtrationThe solids were filtered
  10. washwashed with 10 ml of ether (twice)
  11. customto dry overnight

Sources & evidence

ORD record
ord-e244d18f577e4f42a699ea40c61b630a
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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