Phenyl Isothiocyanate → HCID 53927476, compound

HRID 1417731Notes

Reaction equation

HRID 1417731 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(N(CC)CC)C.[C:14]1([N:20]=[C:21]=[S:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[C:14]1([NH:20][C:21](=[S:22])[NH:2][CH2:3][C:4]([NH2:6])=[O:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 2723639Glycinamide hydrochloride

Product 1

HCID 53927476HCID 53927476, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of glycinamide hydrochloride (8.25 g), triethyl amine (10.0 g), phenyl-isothiocyanate (10.1 g), and methylene chloride (300 mL) was heated at reflux for 1 hour. The mixture was stirred at ambient temperature for 2 hours. The precipitate was collected by filtration, washed with methylene chloride, then with diethyl ether and air dried to give 2-(3-phenyl-thioureido)-acetamide (9.7 g), m.p. 150°-152° C. Anal. Calcd. for. C9H11N3O S: C, 51.66; H, 5.30; N, 20.08. Found: C, 51.41; H, 5.04; N, 20.02. Mass spectrum (EI, M.+) m/z 209. 1H-NMR (DMSO-d6; 400 MHz) δ9.88 (s, 1 H), 7.70 (t, 1 H), 7.52 (s, 1 H), 7.47 (d, 2 H), 7.31 (t, 2 H), 7.15 (s, 1 H), 7.09 (t, 1 H), and 4.08 ppm (d, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with methylene chloride
  5. dry with materialwith diethyl ether and air dried

Sources & evidence

ORD record
ord-92cfde7e186147ae8ae53f9158a0762f
Source dataset
uspto-grants-1999_03
Patent number
US05877324

Reaction notes

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