Sodium Carbonate → HCID 13883826, compound

HRID 543776Notes

Reaction equation

HRID 543776 reaction equation
[F:1][C:2]([F:22])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][C:18]#[N:19])[N:8]=1.C(=O)([O-])[O-:24].[Na+].[Na+]>S(=O)(=O)(O)O>[F:22][C:2]([F:1])([F:21])[CH2:3][N:4]=[C:5]([NH2:20])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9](/[CH:13]=[CH:14]/[CH2:15][CH2:16][CH2:17][C:18]([NH2:19])=[O:24])[N:8]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 20202796HCID 20202796, compound

Product 1

HCID 13883826HCID 13883826, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of trans-6-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]hex-5-enenitrile (400 mg.) in concentrated sulphuric acid (2 ml.) was kept at 20° for 18 hours then added dropwise to saturated aqueous sodium carbonate. The mixture was extracted with EtOAc (2×15 ml.) and the extract dried (MgSO4) and evaporated in vacuo to give trans-6-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]hex-5-enamide as an oil. The maleic acid salt was prepared in acetone (yield 205 mg; 36%), m.p. 177°-179°.

Workup

  1. extractionThe mixture was extracted with EtOAc (2×15 ml.)
  2. dry with materialthe extract dried (MgSO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4f0ad518eaa4a6f835b2edf35cb9851
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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