Sulfuric Acid → HCID 178512754, compound

HRID 1380808Notes

Reaction equation

HRID 1380808 reaction equation
C(=O)(O)O.[I:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:10][C:11]([NH2:13])=[NH:12].[OH:17][S:18]([OH:21])(=[O:20])=[O:19]>O>[S:18]([OH:21])([OH:20])(=[O:19])=[O:17].[I:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=1)[CH2:9][NH:10][C:11]([NH2:13])=[NH:12]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178512753HCID 178512753, compound

Product 1

HCID 178512754HCID 178512754, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the m-iodobenzylguanidine bicarbonate (539 mg, 1.6 mmol) in 5 ml of water was slowly added 0.8 ml (1.6 mEq) of 2N H2SO4. The resulting suspension was warmed to solution and the desired guanidine sulfate crystallized on cooling to room temperature. The colorless crystals were collected, washed with cold water and dried in vacuo: yield 403 mg (78%), mp 164°-167° C. Recrystallization from H2O-EtOH provided m-iodobenzylguanidine sulfate as colorless crystals: mp 166°-167° C.; HPLC [THF/0.1M NaH2PO4 12/88, 3.0 ml/min] showed only one peak tR= 8.6 min; IR (nujol) 3340 (NH), 3160 (NH), 1660 and 1630 (C=N), 1090 (S=0), 780 and 695 cm (1,3-disubstituted benzene); PMR (CD3OD) δ4.36 (S,2,CH2), 6.96-7.73 [m(7 peaks), 4,arom]; the aromatic peak pattern was identical to that observed for m-iodobenzylamine hydrochloride in CD3OD. Anal. Calcd for C8H10IN3 .O.5H2SO4 : C,29.64; H, 3.42. Found C,29.55,H, 3.40.

Workup

  1. temperatureThe resulting suspension was warmed to solution
  2. customthe desired guanidine sulfate crystallized
  3. customThe colorless crystals were collected
  4. washwashed with cold water
  5. customdried in vacuo
  6. customRecrystallization from H2O-EtOH

Sources & evidence

ORD record
ord-b56b0a66b3af4540b90547d052b56911
Source dataset
uspto-grants-1986_04
Patent number
US04584187

Reaction notes

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