Acetonitrile → HCID 70100273, compound

HRID 619018Notes

Reaction equation

HRID 619018 reaction equation
[C:1]1([O:7][C:8]([N:10]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([CH:24]4[C:30]5=[N:31][CH:32]=[C:33]([Br:35])[CH:34]=[C:29]5[CH2:28][CH2:27][C:26]5[CH:36]=[C:37]([Cl:41])[CH:38]=[C:39]([Cl:40])[C:25]4=5)[CH2:20][CH2:19]3)=[O:17])[CH2:11]2)=[NH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC#N.CCN(CC)CC.[CH3:52][NH:53][S:54](Cl)(=[O:56])=[O:55]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[C:1]1([O:7][C:8]([N:10]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([CH:24]4[C:30]5=[N:31][CH:32]=[C:33]([Br:35])[CH:34]=[C:29]5[CH2:28][CH2:27][C:26]5[CH:36]=[C:37]([Cl:41])[CH:38]=[C:39]([Cl:40])[C:25]4=5)[CH2:20][CH2:19]3)=[O:17])[CH2:11]2)=[N:9][S:54](=[O:56])(=[O:55])[NH:53][CH3:52])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 9961224HCID 9961224, compoundHCID 11789235N-Methylsulfamoyl chloride

Product 1

HCID 70100273HCID 70100273, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Disolve the product of Example 9 (1 equivalent) in an inert anhydrous solvent such as CH3CN, benzene or toluene and add Et3N (2 equivalents). Cool the solution to 0° C. and add N-methylsulfamoyl chloride (1.2 equivalents) [prepared as described in: J. A. Kloek and K. L. Leschinsky, J. Org. Chem., 41 (25) (1976), p. 4028-4029]. Stir the mixture at 0° C. to 25° C. for 3 h, extract, filter and evaporate to give the title compound.

Workup

  1. customprepared
  2. extractionextract
  3. filtrationfilter
  4. customevaporate

Sources & evidence

ORD record
ord-0858a55e8c294fcd8811637ddf713f0a
Source dataset
uspto-grants-1999_09
Patent number
US05958890

Reaction notes

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