Phosphorus oxychloride → 5-(4-Iodo-2-methoxyphenyl)-1,3,4-thiadiazol-2-amine

HRID 579349Notes

Reaction equation

HRID 579349 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=O)=[C:4]([O:11][CH3:12])[CH:3]=1.[NH:13]([C:15](=[S:17])[NH2:16])[NH2:14].P(Cl)(Cl)(Cl)=O>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:17][C:15]([NH2:16])=[N:13][N:14]=2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 2723789ThiosemicarbazideHCID 134507564-Iodo-2-methoxybenzoic acid

Product 1

HCID 867271705-(4-Iodo-2-methoxyphenyl)-1,3,4-thiadiazol-2-amineYield 16.2%

Conditions

Temperature
78 °C

Procedure

To an ice cooled mixture of 4-iodo-2-methoxybenzoic acid (6.178 g, 22.22 mmol) and hydrazinecarbothioamide (2.43 g, 26.7 mmol) was added phosphorous oxychloride (6.21 mL, 66.7 mmol) slowly. The mixture was heated at 78° C. overnight. After cooling to 0° C., ice water was added and the mixture was vigorously stirred for 1 hour. The resulting precipitate was filtered, washed with water, and re-suspended in saturated NaHCO3(aq) and water (1:1) for 1 hour. The solid was filtered, washed with water, and dried in vacuo to afford the crude compound. The crude material was purified by flash chromatography (MeOH/CH2Cl2) to afford the title compound (1.2 g, 16% yield). MS m/z 334.0 [M+H]+.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. waitwater (1:1) for 1 hour
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried in vacuo
  8. customto afford the crude compound
  9. customThe crude material was purified by flash chromatography (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f3e988cdb3ba4cc7880dcbeabf01fe88
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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