Hydrochloric Acid → Propyrisulfuron

HRID 1946465Notes

Reaction equation

HRID 1946465 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH3:12])=[N:6][N:5]2[C:13]=1[S:14]([NH2:17])(=[O:16])=[O:15].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([NH:28][C:29](=O)[O:30]C2C=CC=CC=2)[N:21]=1.C1CCN2C(=NCCC2)CC1.Cl>O.C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH3:12])=[N:6][N:5]2[C:13]=1[S:14]([NH:17][C:29]([NH:28][C:22]1[N:21]=[C:20]([O:19][CH3:18])[CH:25]=[C:24]([O:26][CH3:27])[N:23]=1)=[O:30])(=[O:15])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 230281102-Chloro-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide

Product 1

HCID 11990852Propyrisulfuron

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-6-n-propylimidazo[1,2-b]pyridazin-3-ylsulfonamide (0.49 g, 1.78 mmol), phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate (0.55 g, 2 mmol) and acetonitrile (5 ml) were introduced into a 25-ml eggplant type flask and stirred at room temperature, and DBU (0.31 g, 2 mmol) was added all at once thereto, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the reaction solution was poured into water (50 ml) and adjusted to about pH 2 with dilute hydrochloric acid, whereby crystals were formed. The crystals were collected by filtration, washed with water, acetone and ether in this order and dried under reduced pressure to give the title compound as pale brown crystals. The yield was 0.71 g (89.5%).

Workup

  1. stirringwas stirred at room temperature for 3 hours
  2. customwhereby crystals were formed
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water, acetone and ether in this order
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-ead64daa55ca4b748e87921da1d7b6ca
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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