Hydrazine hydrate (1:1) → 1-Ethyl-3-(7-hydrazinocarbonyl-5-pyridin-3-yl-benzothiazol-2-yl)-urea

HRID 1941955Notes

Reaction equation

HRID 1941955 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[S:12][C:11]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[N:10][C:9]=2[CH:8]=[C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=1)=O.O.[NH2:27][NH2:28]>CO.O>[CH2:18]([NH:17][C:15]([NH:14][C:11]1[S:12][C:13]2[C:5]([C:3]([NH:27][NH2:28])=[O:2])=[CH:6][C:7]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[CH:8][C:9]=2[N:10]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 578136192-(3-Ethyl-ureido)-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester

Product 1

HCID 578136141-Ethyl-3-(7-hydrazinocarbonyl-5-pyridin-3-yl-benzothiazol-2-yl)-ureaYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 2-(3-Ethyl-ureido)-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester (319 mg, 0.895 mmol) in methanol (10 ml) was treated with hydrazine hydrate (2 ml) and stirred at ambient temperature for 16 h. HPLC indicated that the reaction mixture still contained a considerable amount of starter so a further 1 ml of hydrazine hydrate was added and the stirring continued for a further 24 h. The resultant mixture was diluted with water (50 ml) and the solid collected by filtration. This was washed with water (25 ml) followed by ethanol (25 ml) and dried in vacuo to give 1-Ethyl-3-(7-hydrazinocarbonyl-5-pyridin-3-yl-benzothiazol-2-yl)-urea as an off-white solid (312 mg, 98%).

Workup

  1. additionwas added
  2. waitthe stirring continued for a further 24 h
  3. filtrationthe solid collected by filtration
  4. washThis was washed with water (25 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e25fd87c77934537833d1919add14afd
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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