4-Fluorophenyl isothiocyanate → HCID 53840358, compound

HRID 1417719Notes

Reaction equation

HRID 1417719 reaction equation
[NH2:1][CH2:2][C:3]([NH2:5])=[O:4].[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[S:15])=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[S:15])[NH:1][CH2:2][C:3]([NH2:5])=[O:4])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 152414-Fluorophenyl isothiocyanateHCID 69020Glycinamide

Product 1

HCID 53840358HCID 53840358, compoundYield 78.6%

Procedure

Glycinamide (5.0 g) and 4-fluorophenyl-isothiocyanate (9.18 g) were stirred in (200 mL). The mixture was heated at reflux for 5 minutes then stirred at ambient temperature for 20 minutes. The precipitated solid was collected by filtration, washed with chloroform and air dried to give 2-[3-(4-fluorophenyl)-thioureido]-acetamide (10.7 g) as a light pink solid, m.p. 168°-170° C. (dec.). Mass spectrum (EI, M.+) m/z 277. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.97 (broad s, 1 H), 7.82 (broad s, 1 H), 7.45-7.52 (m, 3 H), 7.10-7.17 (m, 3 H), and 4.06 ppm (s, 2 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 minutes
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with chloroform and air
  5. customdried

Sources & evidence

ORD record
ord-8590ec2990b44fae9e99f2e5b9509e7e
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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