Hydrazine hydrate (1:1) → HCID 21912551, compound

HRID 1245447Notes

Reaction equation

HRID 1245447 reaction equation
[CH2:1]([NH:8][C:9]([NH:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17][N:18]2C(=O)C3C(=CC=CC=3)C2=O)[N:16]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:18][CH2:17][C:15]1[N:16]=[C:12]([NH:11][C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21912586HCID 21912586, compound

Product 1

HCID 21912551HCID 21912551, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-Benzyl-N′-{4-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-1,3-thiazol-2-yl}urea 20c (3 g; 7.64 mmol) was suspended in 50 ml of CH3OH and then, after addition of 2 g of hydrazine hydrate, stirred at RT for 2 h. The resulting solid was filtered off, and the resulting mother liquor was evaporated and triturated with 0.5 N HCl. Renewed filtration and concentration of the mother liquor led to enrichment of the required product, and this purification step was therefore repeated 3×. 0.78 g; ESI-MS [M+H+]=263.05

Workup

  1. filtrationThe resulting solid was filtered off
  2. customthe resulting mother liquor was evaporated
  3. customtriturated with 0.5 N HCl
  4. filtrationRenewed filtration and concentration of the mother liquor
  5. customthis purification step

Sources & evidence

ORD record
ord-f13176d31f8f4a46a7de4f49e7c08eb7
Source dataset
uspto-grants-2006_10
Patent number
US07125883B1

Reaction notes

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