Sodium hydride → HCID 9933225, compound

HRID 1416235Notes

Reaction equation

HRID 1416235 reaction equation
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([S:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:7][N:8]=1.[CH2:14]([O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[CH2:14]([O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:3][C:4]2[S:5][C:6]([S:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:7][N:8]=2)=[O:30])=[CH:32][CH:33]=1)/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 5839535-[(2-Methylpropyl)thio]-1,3,4-thiadiazol-2-amineHCID 123615004-Geranyloxybenzoic acid

Product 1

HCID 9933225HCID 9933225, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (0.4 g) and 2-amino-5-isobutylthio-1,3,4-thiadiazole (1.1 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 resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 1.9 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 resulting solid was recrystallized from n-hexane/ethanol

Sources & evidence

ORD record
ord-0dca83efaf0b403db2d8199a855153f8
Source dataset
uspto-grants-1999_06
Patent number
US05912258

Reaction notes

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