Sulfuric Acid → HCID 71621928, compound

HRID 871025Notes

Reaction equation

HRID 871025 reaction equation
[C:1]([C:3]1[C:4]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[N:5][S:6][C:7]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:10])#[N:2].S(=O)(=O)(O)[OH:30].[OH-].[NH4+]>>[N+:26]([C:23]1[CH:22]=[CH:21][C:20]([C:4]2[C:3]([C:1]([NH2:2])=[O:30])=[C:7]([NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)=[O:10])[S:6][N:5]=2)=[CH:25][CH:24]=1)([O-:28])=[O:27]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 86689234HCID 86689234, compound

Product 1

HCID 71621928HCID 71621928, compound

Conditions

Temperature
45 °C

Procedure

1-[4-cyano-3-(4-nitrophenyl)isothiazol-5-yl]-3-(3-pyrrolidin-1-ylpropyl)urea (36.0 g) was added portion wise to concentrated sulfuric acid (180.0 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 (2000 ml), stirred for 30 min. The resulting mixture was made basic using ammonium hydroxide, filtered the solid and washed with water then dried in vacuo to give the title compound as off white solid (34.0 g, 90%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered the solid
  3. washwashed with water
  4. customthen dried in vacuo

Sources & evidence

ORD record
ord-b8ade2eca09c4d87bb7984a611849cb9
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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