Acetic Acid → HCID 69793526, compound

HRID 1071554Notes

Reaction equation

HRID 1071554 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH:11][CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1.C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>Br.O>[OH2:11].[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1.[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 11159325(2-Aminopyridin-3-yl)methanolHCID 178527775HCID 178527775, compound

Product 1

HCID 69793526HCID 69793526, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A mixture of 9.6 g (63 mmole) of 2-mercaptobenzimidazole and 7.7 g (62 mmole) of 3-hydroxymethyl-2-pyridinamine was dissolved in 60 ml of 48% aqueous hydrobromic acid and 60 ml of acetic acid and heated to reflux. After being cooled to room temperature, the mixture was poured into water and made alkaline with potassium carbonate. The oil that separated solidified upon addition of diethyl ether to the aqueous mixture. The solid was collected by filtration, washed with portions of diethyl ether and water, and air dried to yield 12.4 g of the title compound as an analytically pure hemihydrate. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis. Analysis. Calc'd. for C13H12N4S*½H2O: C,58.84; H, 4.93; N, 21.11; S, 12.08. Found: C, 59.06; H, 4.48; N, 20.82; S, 12.16.

Workup

  1. customThe oil that separated
  2. additionsolidified upon addition of diethyl ether to the aqueous mixture
  3. filtrationThe solid was collected by filtration
  4. washwashed with portions of diethyl ether and water, and air
  5. customdried

Sources & evidence

ORD record
ord-6279ff5a2c324d74a795a1d6600f042c
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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