Methoxyacetic Acid → 5-(Methoxymethyl)-1,3,4-thiadiazol-2-amine

HRID 372270

Reaction equation

HRID 372270 reaction equation
P(Cl)(Cl)(Cl)=O.[NH2:6][NH:7][C:8]([NH2:10])=[S:9].[CH3:11][O:12][CH2:13][C:14](O)=O.[OH-].[Na+]>>[NH2:10][C:8]1[S:9][C:14]([CH2:13][O:12][CH3:11])=[N:6][N:7]=1

Participants

5

Reactant 4

HCID 12251Methoxyacetic AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2723789Thiosemicarbazide

Product 1

HCID 6608445-(Methoxymethyl)-1,3,4-thiadiazol-2-amineYield 69.8%

Procedure

Phosphoryl chloride (87 ml) was added dropwise to a vigorously stirred mixture of thiosemicarbazide (100 g), methoxyacetic acid (100 g) and petroleum ether b.p. 80°-100° (200 ml) maintained at 60°-70°. The temperature of the mixture was slowly raised to 95° and was kept at this temperature until the evolution of gas ceased. The solvent was evaporated and the residual syrup was dissolved in water (200 ml) to give a yellow solution which was adjusted to pH 7 by the addition of 10N NaOH. The mixture was filtered to give 5-amino-2-methoxymethyl-(1,3,4)-thiadiazole (111.25 g). Recrystallisation from water gave compound with m.p. 177°-179°.

Workup

  1. temperaturemaintained at 60°-70°
  2. temperatureThe temperature of the mixture was slowly raised to 95°
  3. customThe solvent was evaporated
  4. dissolutionthe residual syrup was dissolved in water (200 ml)
  5. customto give a yellow solution which
  6. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-a4f9c888935b464f8be10d5ae0b6a9f1
Source dataset
uspto-grants-1978_05
Patent number
US04090026

Linked notes

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