Water → HCID 86687865, compound

HRID 1910463Notes

Reaction equation

HRID 1910463 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][C:9](O)=O)[CH2:3][C:4](O)=O.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].O.[OH-].[Na+]>O=P(Cl)(Cl)Cl>[CH3:1][CH:2]([CH2:7][CH2:8][C:9]1[S:15][C:14]([NH2:16])=[N:13][N:12]=1)[CH2:3][C:4]1[S:15][C:14]([NH2:16])=[N:13][N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 122923-Methylhexanedioic acidHCID 14798Sodium HydroxideHCID 2723789Thiosemicarbazide

Product 1

HCID 86687865HCID 86687865, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methyl adipic acid (5.00 g, 31.22 mmol) and thiosemicarbazide (5.69 g, 62.43 mmol) in POCl3 (45 mL) was heated at 90° C. for 4 h. The reaction was cooled to room temperature and poured into a mixture of ice and water. Sodium hydroxide pellets were added to the mixture until it was basic (pH 14). The white precipitate was collected by suction filtration, rinsed with water and dried to provide 5,5′-(2-methylbutane-1,4-diyl)-bis(1,3,4-thiadiazol-2-amine) (1003, 8.97 g). 1H NMR (300 MHz, DMSO-d6) δ 7.00 (s, 4H), 2.89-2.81 (m, 3H), 2.89-2.81 (m, 3H), 2.69 (dd, J=7.6, 7.6 Hz, 1H), 1.89-1.46 (m, 3H), 0.94 (d, J=6.6 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe white precipitate was collected by suction filtration
  3. washrinsed with water
  4. customdried

Sources & evidence

ORD record
ord-42aa46ffed48413bb1040dc8518d7c6d
Source dataset
uspto-grants-2013_12
Patent number
US08604016B2

Reaction notes

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