Sodium hydride → HCID 67598086, compound

HRID 1416232Notes

Reaction equation

HRID 1416232 reaction equation
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([S:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:7][N:8]=1.[CH2:19]([O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[CH2:19]([O:29][C:30]1[CH:31]=[CH:32][C:33]([C:34]([NH:3][C:4]2[S:5][C:6]([S:9][CH2:10][CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:7][N:8]=2)=[O:35])=[CH:37][CH:38]=1)/[CH:20]=[C:21](/[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])\[CH3:22]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 123615004-Geranyloxybenzoic acidHCID 54007829HCID 54007829, compound

Product 1

HCID 67598086HCID 67598086, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.4 g) and 2-amino-5-piperidinopropylthio-1,3,4-thiadiazole (1.6 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes while being cooled with ice. 4-Geranyloxybenzoic acid (1.6 g) and carbonyldiimidazole (1.1 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes at room temperature and the mixture was added to the former reaction mixture. The mixture was stirred for 4 hours at room temperature, and then concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1). The resulting solid was recrystallized from n-hexane/ethanol, hereby yielding 2.1 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. additionthe mixture was added to the former reaction mixture
  3. concentrationconcentrated under a vacuum
  4. additionThe residue, with water added
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe extract was dried over sodium sulfate anhydride
  7. concentrationconcentrated under a vacuum
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1)
  9. customThe resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-bed0bd556ecb4ea89f147fcfc6a14b2c
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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