Sulfuric Acid → 3-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amide

HRID 871007Notes

Reaction equation

HRID 871007 reaction equation
[C:1]([C:3]1[C:4]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15](OC)=[O:16])=[O:10])#[N:2].S(=O)(=O)(O)[OH:29]>>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([C:4]2[C:3]([C:1]([NH2:2])=[O:29])=[C:7]([NH:8][C:9]([N:11]3[CH2:12][CH2:13][CH2:14][C:15]3=[O:16])=[O:10])[S:6][N:5]=2)=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86689227Methyl 4-[({[4-cyano-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]butanoate

Product 1

HCID 716216273-(4-Nitro-phenyl)-5-[(2-oxo-pyrrolidine-1-carbonyl)-amino]-isothiazole-4-carboxylic acid amideYield 99%

Conditions

Temperature
45 °C

Procedure

Methyl 4-[({[4-cyano-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]butanoate (10.0 g) was added portion wise to concentrated sulfuric acid (50.0 mL) at ambient temperature over 20 min. The resulting suspension was heated to 45° C. over 90 min. The reaction mixture was cooled to ambient temperature. The reaction mixture was poured into ice water (600 ml), stirred for 30 min. The solid which formed was collected and washed with water then dried in vacuo to give the titlee compound as off white solid (10.2 g, 99%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customThe solid which formed
  3. customwas collected
  4. washwashed with water
  5. customthen dried in vacuo

Sources & evidence

ORD record
ord-0fa5f32a13df4320ba790b44f8e26357
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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