Sulfuric Acid → 5-(3-(3-Methoxypropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide

HRID 870997Notes

Reaction equation

HRID 870997 reaction equation
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])=[O:10])#[N:2].[OH:26]S(O)(=O)=O>>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([NH:8][C:7]1[S:6][N:5]=[C:4]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[C:3]=1[C:1]([NH2:2])=[O:26])=[O:10]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 866892211-(4-Cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-methoxypropyl)urea

Product 1

HCID 716208355-(3-(3-Methoxypropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamide

Conditions

Temperature
45 °C

Procedure

A mixture of 1-(4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-methoxypropyl)urea (12 mg, 0.032 mmol) in 0.8 mL conc. H2SO4 was heated at 45° C. After 1.5 hours the reaction was quenched into 25 mL water containing brine. The aqueous solution was adjusted to pH=1 using saturated NaHCO3 and then extracted with EtOAc, the EtOAc layer washed with brine, dried with anhydrous Na2SO4 and rotary evaporated to a solid. The solid was recrystallized from acetonitrile giving the title compound as a white solid (4 mg, 29%).

Workup

  1. customAfter 1.5 hours the reaction was quenched into 25 mL water
  2. additioncontaining brine
  3. extractionextracted with EtOAc
  4. washthe EtOAc layer washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customrotary evaporated to a solid
  7. customThe solid was recrystallized from acetonitrile giving the title compound as a white solid (4 mg, 29%)

Sources & evidence

ORD record
ord-49b51b5a00a0429dbcf435e2449851b6
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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