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Methanol → HCID 14628047, compound

HRID 2165936
Notes
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Reaction equation

HRID 2165936 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[NH:14][C:15]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:38](OC(=O)C)(=[O:40])[CH3:39].CO>CN(C)C1C=CN=CC=1.ClCCl>[C:38]([O:30][C:5]1[C:6]([CH2:27][CH2:28][CH3:29])=[C:7]([CH:25]=[CH:26][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[NH:14][C:15]2[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][C:16]=2[N:17]=1)(=[O:40])[CH3:39]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 14628044HCID 14628044, compound

Product 1

HCID 14628047HCID 14628047, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propylthio]benzimidazole-5-carboxylic acid (1.50 g), triethylamine (4 ml), acetic anhydride (4 ml) and 4-dimethylaminopyridine (100 mg) in dichloromethane (50 ml) was stirred at 0 ° C. and then at room temperature for 5 hours. Methanol (4 ml) was added to the mixture, further stirred for an additional 30 minutes and then the mixture was evaporated. The residue was washed with water, dissolved in ethanol, and concentrated to dryness. The residue was purified by silica gel column chromatography, eluting with dichloromethane-ethyl acetate-methanol (10:2:1), and recrystallized from n-hexane-chloroform to give the title compound (970 mg, 58.2%) as yellow crystals, mp 85-87 ° C.

Workup

  1. stirringfurther stirred for an additional 30 minutes
  2. customthe mixture was evaporated
  3. washThe residue was washed with water
  4. dissolutiondissolved in ethanol
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane-ethyl acetate-methanol (10:2:1)
  8. customrecrystallized from n-hexane-chloroform

Sources & evidence

ORD record
ord-a2ba410fe5704132a3db71ef8a4e6b17
Source dataset
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04942245

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes