HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Imidazole → 2-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide

HRID 1393854
Notes
Print preview

Reaction equation

HRID 1393854 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N1C=CN=C1)(N1C=CN=C1)=O.N1C=CN=C1.[H-].[Na+].[NH2:39][C:40]1[S:41][S:42][C:43](=[S:45])[N:44]=1>O1CCCC1.O>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:39][C:40]2[S:41][S:42][C:43](=[S:45])[N:44]=2)=[O:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 123873512-[4-(Octyloxy)phenyl]acetic acid

Product 1

HCID 596805052-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide
Yield 21.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-[4-(Octyloxy)phenyl]acetic acid (0.900 g, 3.40 mmol) was dissolved in tetrahydrofuran (11 ml), and 1,1′-carbonyldiimidazole (0.622 g, 4.09 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at 0° C. Sodium hydride (60% oil suspension 0.136 g, 3.40 mmol) was suspended in tetrahydrofuran (11 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.511 g, 3.40 mmol) was added thereto. After being stirred for 30 minutes at 0° C., the reaction mixture, with the imidazole mixture added thereto, was stirred for 3 hours at 0° C. The mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel column chromatography (chloroform), to give 2-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 6) (0.290 g, 21%).

Workup

  1. stirringwas stirred for 3 hours at 0° C
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-b5e92dda736a4f58a3e179df992b4852
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07348017B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes