Water → HCID 14880505, compound

HRID 1588842Notes

Reaction equation

HRID 1588842 reaction equation
[NH2:1][CH2:2][C:3]([N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:18][S:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].O.[O:28]1CCC[CH2:29]1>>[CH3:18][S:19][C:20]1[CH:21]=[C:22]([NH:23][C:29](=[O:28])[NH:1][CH2:2][C:3]([N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:4])[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 15693Benzenamine, 3-(methylthio)-HCID 14880491HCID 14880491, compound

Product 1

HCID 14880505HCID 14880505, compound

Procedure

N,N,'-Carbonyldiimidazole (0.72 g) is added to a solution of 2-amino-N,N-diphenylacetamide (1 g) in anhydrous tetrahydrofuran (15 cc). The solution is stirred for 2 hours at a temperature in the region of 25° C. and 3-methylthioaniline (1.2 g) is then added. The solution obtained is stirred under reflux for 12 hours and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is taken up with distilled water (60 cc) and stirred for 30 minutes at a temperature in the region of 20° C. The insoluble product is separated by filtration, washed with distilled water and dried in the air. After recrystallization in acetonitrile, 2-[3-(3-methylthiophenyl)ureido]-N,N-diphenylacetamide (1 g), m.p. 182° C., is obtained.

Workup

  1. additionis then added
  2. customThe solution obtained
  3. temperatureunder reflux for 12 hours
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. customThe residue obtained
  6. stirringstirred for 30 minutes at a temperature in the region of 20° C
  7. customThe insoluble product is separated by filtration
  8. washwashed with distilled water
  9. customdried in the air
  10. customAfter recrystallization in acetonitrile

Sources & evidence

ORD record
ord-9b4fc8d0caca47209d5327bca3b86bcb
Source dataset
uspto-grants-1993_06
Patent number
US05223529

Reaction notes

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