N'-(3-butyl-5-tert-butyl-1,3,4-thiadiazol-3-ium-2-yl)-N,N-dimethylmethanimidamide bromide → 5-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine

HRID 2064508Notes

Reaction equation

HRID 2064508 reaction equation
[Br-].[C:2]([C:6]1[S:10][C:9](/[N:11]=C/N(C)C)=[N+:8]([CH2:16][CH2:17][CH2:18][CH3:19])[N:7]=1)([CH3:5])([CH3:4])[CH3:3]>Cl>[C:2]([C:6]1[S:10][C:9](=[NH:11])[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[N:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

3

Reactant 1

HCID 136375772N'-(3-butyl-5-tert-butyl-1,3,4-thiadiazol-3-ium-2-yl)-N,N-dimethylmethanimidamide bromide

Product 1

HCID 666433495-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of Example 16B (4 g, 11.45 mmol) in HCl (1 N, 12.6 mL) was heated at 65° C. for 12 hours. The mixture was cooled at room temperature and extracted with ether (2×20 mL). The aqueous phase was neutralized to pH 7 with concentrated ammonia and extracted with ether (2×25 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hexanes-EtOAc: 0-80%) to give the title compound. LC/MS m/z 214 (M+H)+.

Workup

  1. extractionextracted with ether (2×20 mL)
  2. extractionextracted with ether (2×25 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hexanes-EtOAc: 0-80%)

Sources & evidence

ORD record
ord-f56e0d4d828b46449cf4cba1e5a7351f
Source dataset
uspto-grants-2012_10
Patent number
US08288428B2

Reaction notes

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