Water → Hydrochloric Acid

HRID 237067Notes

Reaction equation

HRID 237067 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[NH:17][C:16](=[O:18])[C:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=2)=[CH:14][N:13]=1.B(Br)(Br)Br.O.[Cl:33]CCl>>[ClH:33].[ClH:33].[ClH:33].[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]1[NH:17][C:16](=[O:18])[C:15]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 3047307HCID 3047307, compound

Product 2

HCID 313Hydrochloric AcidHCID 30537044(1H)-Pyrimidinone, 5-((3-hydroxyphenyl)methyl)-2-((2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl)amino)-, dihydrochloride

Procedure

2-[2-(5-Methyl-4-imidazolylmethylthio)ethylamino]-5-(3-methoxybenzyl)-4-pyrimidone (2.35 g) was suspended in dry dichloromethane (30 ml) and boron tribromide (6.49 g) carefully added. The mixture was stirred in a dry atmosphere overnight. Careful addition of water (30 ml) was followed by separation of the two phases. The aqueous phase was treated in NaHCO3 which precipitated a tacky solid which was repeatedly washed with water until it became solid, when it was filtered and dried. Treatment with ethanolic HCl gave 2-[2-(5-methyl- 4-imidazolylmethylthio)ethylamino]-5-(3-hydroxybenzyl)-4-pyrimidone dihydrochloride, m.p. 142°-144° (ex. ethanol)

Workup

  1. customwas followed by separation of the two phases
  2. additionThe aqueous phase was treated in NaHCO3 which
  3. customprecipitated a tacky solid which
  4. washwas repeatedly washed with water until it
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-caa69e26a77d4e22b86a73f1f72c02e2
Source dataset
uspto-grants-1979_06
Patent number
US04159329

Reaction notes

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