Phosphorus oxychloride → HCID 43805572, compound

HRID 579372Notes

Reaction equation

HRID 579372 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([Cl:11])[CH:3]=1.[NH:12]([C:14](=[S:16])[NH2:15])[NH2:13].P(Cl)(Cl)(Cl)=O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:16][C:14]([NH2:15])=[N:12][N:13]=2)=[C:4]([Cl:11])[CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 1088294-Bromo-2-chlorobenzoic acidHCID 2723789Thiosemicarbazide

Product 1

HCID 43805572HCID 43805572, compoundYield 64.8%

Conditions

Temperature
78 °C

Procedure

To an ice-cooled mixture of 4-bromo-2-chlorobenzoic acid (3 g, 12.74 mmol) and hydrazinecarbothioamide (2.17 g, 23.81 mmol) was added phosphorous oxychloride (3.56 mL, 38.2 mmol) slowly. The mixture was heated at 78° C. overnight. After cooling to 0° C., ice water was added. The mixture was vigorously stirred for 1 h. The resulting precipitate was filtered and washed with water then re-suspended in a saturated NaHCO3 solution and water (1:1) for 1 h. The solid was filtered, washed with water, and concentrated in vacuo to give 5-(4-bromo-2-chlorophenyl)-1,3,4-thiadiazol-2-amine (2.4 g, MS: 291.8 [M+H+].)

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. waitthen re-suspended in a saturated NaHCO3 solution and water (1:1) for 1 h
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad2895f70e724d8ba92415aaa68876c9
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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