Hydrochloric Acid → HCID 20148320, compound

HRID 568998Notes

Reaction equation

HRID 568998 reaction equation
N[C:2]1[S:3][C:4]([C:7]([F:13])([F:12])[S:8][CH:9]([CH3:11])[CH3:10])=[N:5][N:6]=1.N([O-])=O.[Na+].[ClH:18]>C(O)(=O)C.O>[Cl:18][C:2]1[S:3][C:4]([C:7]([F:13])([F:12])[S:8][CH:9]([CH3:11])[CH3:10])=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 20148322HCID 20148322, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20148320HCID 20148320, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

2-Amino-5-[difluoro(isopropylthio)methyl]-1,3,4-thiadiazole (190 g) was dissolved in a mixture of acetic acid (880 ml) and concentrated hydrochloric acid (216.5 ml) at 60° C. A solution of sodium nitrite (171.3 g) in water (300 ml) was then added dropwise over 30 minutes at 65°-70° C. The mixture was stirred at 65° C. for 15 minutes and then allowed to cool. It was then poured onto water (3 L) and extracted with ether, the combined extracts being washed with water, dried (MgSO4) and evaporated to give an orange liquid, which was distilled under vacuum to give 150 g of 2-chloro-5-[difluoro(isopropylthio)methyl]-1,3,4-thiadiazole, bp 75°-77° C. at 0.7 mmHg.

Workup

  1. temperatureto cool
  2. additionIt was then poured onto water (3 L)
  3. extractionextracted with ether
  4. washthe combined extracts being washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an orange liquid, which
  8. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-a00eb3c3c6e84237b987fffe9d1b3b5d
Source dataset
uspto-grants-1988_03
Patent number
US04731105

Reaction notes

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