Hydrogen Bromide → HCID 13178489, compound

HRID 1981447Notes

Reaction equation

HRID 1981447 reaction equation
CS(O)(=O)=O.C(OC([NH:16][CH2:17][C:18]1[CH:37]=[CH:36][C:21]([C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][C:26]=2[O:34][CH3:35])=[O:23])=[CH:20][CH:19]=1)=O)C1C=CC=CC=1.C1(OC)C=CC=CC=1.Br>C(O)(=O)C>[NH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[NH:32])[NH2:33])=[CH:27][C:26]=2[O:34][CH3:35])=[O:23])=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 7519AnisoleHCID 20247179HCID 20247179, compound

Product 1

HCID 13178489HCID 13178489, compoundYield 129.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 1.5 g of 4-amidino-2-methoxyphenyl 4-benzyloxycarbonylaminomethylbenzoate methanesulfonate, was added 15 ml of acetic acid followed by 1 ml of anisole. To the mixture, while being cooled in ice, was added 3.0 ml of an acetic acid solution containing 30% of hydrogen bromide. The mixture was then stirred overnight at room temperature. The insoluble substance precipitated from the reaction mixture was collected by filtration and recrystallized from a methanol-ethyl ether mixture to obtain 1.1 g of colorless crystals of 4-amidino-2-methoxyphenyl 4-aminomethylbenzoate dihydrobromide.

Workup

  1. temperatureTo the mixture, while being cooled in ice
  2. customThe insoluble substance precipitated from the reaction mixture
  3. filtrationwas collected by filtration
  4. customrecrystallized from a methanol-ethyl ether mixture

Sources & evidence

ORD record
ord-0387d0b5b14f4f2381f894d1a9f296a4
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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