Sulfuric Acid → HCID 71621782, compound

HRID 871012Notes

Reaction equation

HRID 871012 reaction equation
[C:1]([C:3]1[C:4]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])#[N:2].S(=O)(=O)(O)[OH:28]>>[NH2:2][C:1]([C:3]1[C:4]([C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])=[O:28]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86689229HCID 86689229, compound

Product 1

HCID 71621782HCID 71621782, compound

Conditions

Temperature
45 °C

Procedure

Methyl 3-[({[4-cyano-3-(4-nitrophenyl)isothiazol-5-yl]amino}carbonyl)amino]propanoate (36.0 g) was added portion wise to concentrated sulfuric acid (150.0 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 by filtration and washed with water then dried in vacuo to give the title compound as an off white solid (28.0 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-c1d6ee6f8ef7435cbf8cca2f5ed3dd80
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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