Thiosemicarbazide → HCID 86719087, compound

HRID 572909Notes

Reaction equation

HRID 572909 reaction equation
[C@@H:1]1([CH2:7][C:8]#[N:9])[CH2:3][C@H:2]1[CH2:4][C:5]#[N:6].N[NH:11][C:12]([NH2:14])=[S:13]>C(O)(C(F)(F)F)=O>[C@@H:1]1([CH2:7][C:8]2[S:13][C:12]([NH2:14])=[N:11][N:9]=2)[CH2:3][C@H:2]1[CH2:4][C:5]1[S:13][C:12]([NH2:14])=[N:11][N:6]=1

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 86719088HCID 86719088, compound

Product 1

HCID 86719087HCID 86719087, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
100 °C

Procedure

trans-2,2′-(cyclopropane-1,2-diyl)diacetonitrile I-4 (1 equivalent) was dissolved in TFA (2.0 mL) and thiosemicarbazide (2 equivalents) was added to it. The reaction mixture was refluxed for 3 h at 100° C. before quenching by careful addition of a saturated solution of NaHCO3 at 0° C. to bring the pH around 8-9. The solid precipitated was filtered and further purified to obtain trans-5,5′-(-cyclopropane-1,2-diylbis(methylene))bis(1,3,4thiadiazol2-amine) I-5.

Workup

  1. custombefore quenching by careful addition of a saturated solution of NaHCO3 at 0° C.
  2. customThe solid precipitated
  3. filtrationwas filtered
  4. customfurther purified

Sources & evidence

ORD record
ord-ed9d598803744663884b470e5a9959b7
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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