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

HRID 870992Notes

Reaction equation

HRID 870992 reaction equation
[C:1]([C:3]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:10])#[N:2].[OH:30]S(O)(=O)=O>>[N:15]1([CH2:14][CH2:13][CH2:12][NH:11][C:9]([NH:8][C:7]2[S:6][N:5]=[C:4]([C:21]3[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=3)[C:3]=2[C:1]([NH2:2])=[O:30])=[O:10])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 866892181-(4-Cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-morpholinopropyl)urea

Product 1

HCID 716230305-(3-(3-Morpholinopropyl)ureido)-3-(4-nitrophenyl)isothiazole-4-carboxamideYield 100%

Conditions

Temperature
45 °C

Procedure

A mixture of 1-(4-cyano-3-(4-nitrophenyl)isothiazol-5-yl)-3-(3-morpholinopropyl)urea (113 mg, 0.27 mmol) in 3.5 mL conc. H2SO4 was heated at 45° C. After 1.5 hours the reaction was quenched into 100 mL ice water giving a white gel-like solid. The aqueous solution was made basic using Na2CO3 and then extracted with EtOAc, the EtOAc layer washed with brine, dried with anhydrous Na2SO4 and rotary evaporated giving the title compound as a light beige solid (118 mg, 100%).

Workup

  1. customAfter 1.5 hours the reaction was quenched into 100 mL ice water giving a white gel-like solid
  2. extractionextracted with EtOAc
  3. washthe EtOAc layer washed with brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary
  5. customevaporated

Sources & evidence

ORD record
ord-eed923d9460b450ea6b6a8a0f816f41e
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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