Thionyl Chloride → HCID 67782192, compound

HRID 2259959Notes

Reaction equation

HRID 2259959 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.[F:16][C:17]([F:35])([F:34])[S:18][C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:22]=[CH:23][CH:24]=1.S(Cl)(Cl)=O>>[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[NH:10][CH2:11][C:12]([N:25]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:18][C:17]([F:35])([F:16])[F:34])[CH:20]=2)=[O:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 54412221HCID 54412221, compound

Product 1

HCID 67782192HCID 67782192, compoundYield 16.1%

Procedure

Using a procedure similar to that described in Example 17, but starting with 2-[(3-methylphenyl)ureido]acetic acid (2.08 g), tert-butyl 2-[(3-trifluoromethylthiophenyl)amino]acetate (3.07 g) and sulphinyl chloride (1.3 g), and after recrystallisation in diisopropyl ether, tert-butyl 2-{2-[3-(3-methylphenyl)ureido]-N-(3-trifluoromethylthiophenyl)acetamido}acetate (0.8 g), m.p. 112° C., is obtained.

Workup

  1. customafter recrystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-41151656db1842059c9bde002d057d18
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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