Water → HCID 68683958, compound

HRID 1713724Notes

Reaction equation

HRID 1713724 reaction equation
[O:1]([CH2:21][CH2:22][NH:23][C:24]([C:26]1[S:27][C:28]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([N+:37]([O-])=O)[C:29]=2[N:30]=1)=[O:25])[CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([N+:18]([O-])=O)[C:10]=2[N:11]=1)=[O:6].O>Cl>[O:1]([CH2:21][CH2:22][NH:23][C:24]([C:26]1[S:27][C:28]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([NH2:37])[C:29]=2[N:30]=1)=[O:25])[CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][C:9]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([NH2:18])[C:10]=2[N:11]=1)=[O:6]

Participants

4

Reactant 2

HCID 962WaterHCID 86615732HCID 86615732, compound

Product 1

HCID 68683958HCID 68683958, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

0.33 g (1.5 mmol; 3.4 eq.) of dihydrated tin chloride is added to 250 mg (0.43 mmol) of N,N′-(oxydiethane-2,1-diyl)bis(5-methoxy-4-nitro-1,3-benzothiazole-2-carboxamide) in solution in 10 ml of concentrated hydrochloric acid. The reaction medium is maintained under stirring at 60° C. for 4 hours, then poured into iced water and neutralized with a SN soda solution. The expected product is then extracted with 3 times 25 ml of dichloromethane, then the organic phases are combined, dried over magnesium sulphate and the is solvent evaporated off under reduced pressure. 220 mg of the expected product (gross yield=98%) is obtained in the form of a yellow oil and is used in the following stage without other purification.

Workup

  1. temperatureThe reaction medium is maintained
  2. extractionThe expected product is then extracted with 3 times 25 ml of dichloromethane
  3. dry with materialdried over magnesium sulphate
  4. customthe is solvent evaporated off under reduced pressure

Sources & evidence

ORD record
ord-1b4ee35939934841a3326056e65dba37
Source dataset
uspto-grants-2010_09
Patent number
US07795284B2

Reaction notes

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