Methanol → HCID 11686114, compound

HRID 1713725Notes

Reaction equation

HRID 1713725 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[O:7]([CH2:26][CH2:27][NH:28][C:29]([C:31]1[S:32][C:33]2[C:39](=[O:40])[CH:38]=[C:37](OC)[C:36](=[O:43])[C:34]=2[N:35]=1)=[O:30])[CH2:8][CH2:9][NH:10][C:11]([C:13]1[S:14][C:15]2[C:21](=[O:22])[CH:20]=[C:19](OC)[C:18](=[O:25])[C:16]=2[N:17]=1)=[O:12].CO>C(O)C.ClCCl>[O:7]([CH2:8][CH2:9][NH:10][C:11]([C:13]1[S:14][C:15]2[C:21](=[O:22])[CH:20]=[C:19]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[C:18](=[O:25])[C:16]=2[N:17]=1)=[O:12])[CH2:26][CH2:27][NH:28][C:29]([C:31]1[S:32][C:33]2[C:39](=[O:40])[CH:38]=[C:37]([NH:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])[C:36](=[O:43])[C:34]=2[N:35]=1)=[O:30]

Participants

6

Reactant 3

HCID 887MethanolHCID 66053N,N-DimethylethylenediamineHCID 68686579HCID 68686579, compound

Product 1

HCID 11686114HCID 11686114, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

81 μl (0.73 mmol; 2 eq.) of N,N-dimethylethylenediamine is added to 200 mg of N,N′-(oxydiethane-2,1-diyl)bis(5-methoxy-4,7-dioxo-4,7-dihydro-1,3-benzothiazole-2-carboxamide) in solution in 300 ml of anhydrous ethanol. The reaction mixture is stirred at 60° C. for 4 hours then the solvent is evaporated off under reduced pressure. The residue is purified on a silica column (eluent: methanol in dichloromethane: gradient of 0 to 20% over 30 minutes then for 15 minutes with 20% of methanol in dichloromethane) and 12 mg (yield=5%) of expected compound is obtained in the form of a red powder.

Workup

  1. customthe solvent is evaporated off under reduced pressure
  2. customThe residue is purified on a silica column (eluent
  3. waitmethanol in dichloromethane: gradient of 0 to 20% over 30 minutes

Sources & evidence

ORD record
ord-30c5d00391354549aeadd102b0f5a351
Source dataset
uspto-grants-2010_09
Patent number
US07795284B2

Reaction notes

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