Dichloromethane → HCID 178456959, compound

HRID 1066104Notes

Reaction equation

HRID 1066104 reaction equation
[CH:1]([NH:4][C:5]1[NH:10][C:9]2[CH:11]=[C:12]([CH2:15][C:16]([O:18]CC)=O)[CH:13]=[CH:14][C:8]=2[S:7](=[O:22])(=[O:21])[N:6]=1)([CH3:3])[CH3:2].[CH:23]1([C:26](=[N:28]O)[NH2:27])[CH2:25][CH2:24]1.[H-].[Na+].ClCCl>CN(C)C=O.C(O)(=O)C>[CH:23]1([C:26]2[N:28]=[C:16]([CH2:15][C:12]3[CH:13]=[CH:14][C:8]4[S:7](=[O:21])(=[O:22])[N:6]=[C:5]([NH:4][CH:1]([CH3:2])[CH3:3])[NH:10][C:9]=4[CH:11]=3)[O:18][N:27]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 178470588HCID 178470588, compound

Product 1

HCID 178456959HCID 178456959, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl (3-isopropylamino-1,1-dioxo-1,4-dihydro-1λ6,2,4-benzothiadiazin-6-yl)acetate (0.20 g), crushed 4 Å molecular sieves (0.6 g), cyclopropanecarboxamide oxime (0.30 g), and sodium hydride (40 mg of a 60% oil dispersion) in 5 ml of dry dimethylformamide was stirred at room temperature for 45 min. Two drops of glacial acetic acid and 20 ml of dichloromethane were added and the mixture was stirred for 10 min. and filtered through celite. The solvents were removed in vacuo from the filtrate. The remaining oil was stirred with 5 ml of water for 15 min and the resulting precipitate was collected by filtration and dried to give the title compound; m.p. 255-259° C.

Workup

  1. stirringthe mixture was stirred for 10 min.
  2. filtrationfiltered through celite
  3. customThe solvents were removed in vacuo from the filtrate
  4. stirringThe remaining oil was stirred with 5 ml of water for 15 min
  5. filtrationthe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ff88bed06de84341a94d0596d9e542d3
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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