Thionyl Chloride → HCID 18951109, compound

HRID 1492499Notes

Reaction equation

HRID 1492499 reaction equation
[NH:1]([CH2:8][C:9]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[NH:26][CH2:27][C:28](O)=[O:29])[CH:21]=[CH:22][CH:23]=1.S(Cl)(Cl)=O>>[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][C:25](=[O:31])[NH:26][CH2:27][C:28]([N:1]([CH2:8][C:9]([O:11][CH2:12][C:13]([F:14])([F:15])[F:16])=[O:10])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:29])[CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 18951146HCID 18951146, compound

Product 1

HCID 18951109HCID 18951109, compoundYield 14.4%

Procedure

The procedure is carried out in a manner analogous to that described in Example 1, but using 2.3 g of 2,2,2-trifluoroethyl 2-anilinoacetate, 2.1 g of 2-[3-(3-methylphenyl)ureido]acetic acid and 0.7 cm3 of thionyl chloride as starting materials. The product obtained is purified by chromatography on 40 g of silica (0.063-0.200 mm) contained in a column 1.5 cm in diameter [eluent: methylene chloride/ethanol (98/2 by volume)], collecting 10-cm3 fractions. Fractions 5 to 8 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. After recrystallization from diisopropyl ether, 0.6 g of 2,2,2-trifluoroethyl 2-{2-[3-(3-methylphenyl)ureido]-N-phenylacetamido}acetate melting at 172° C. is obtained.

Workup

  1. customThe product obtained
  2. customis purified by chromatography on 40 g of silica (0.063-0.200 mm)
  3. customcollecting 10-cm3 fractions
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  5. customAfter recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-635ece8afc5a4432ac34ef05cbc24067
Source dataset
uspto-grants-1994_12
Patent number
US05374656

Reaction notes

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