Hydrochloric Acid → HCID 58930373, compound

HRID 852440Notes

Reaction equation

HRID 852440 reaction equation
CN(C=[N:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([N:18]=[CH:19]N(C)C)=[S:17])[CH:10]=1)(=[O:8])=[O:7])C.[CH2:23](Br)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].Cl.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:24]([C:23]1[S:17][C:16]([NH:15][C:11]2[CH:10]=[C:9]([S:6]([NH2:5])(=[O:7])=[O:8])[CH:14]=[CH:13][CH:12]=2)=[N:18][CH:19]=1)(=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 72466434HCID 72466434, compound

Product 1

HCID 58930373HCID 58930373, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 44 mg (0.13 mmol) N-Dimethylaminomethylene-3-(3-dimethylaminomethylene-thioureido)-benzenesulfonamide and 26 mg (0.13 mmol) phenacyl bromide in 0.8 ml DMF was stirred for 16 h at room temperature. 0.12 ml HCl (37%) was added and the mixture was stirred for 69 h at 100° C. After addition of 0.12 ml N,N-Diisopropylethylamine the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. Evaporation of the product fractions yielded 6 mg (13%) of the title compound.

Workup

  1. stirringthe mixture was stirred for 69 h at 100° C
  2. customHPLC separation on reversed phase
  3. washeluting with an acetonitrile/water gradient
  4. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-40df75e2e35f4567bb02fb3491f7786a
Source dataset
uspto-grants-2007_08
Patent number
US07253197B2

Reaction notes

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