Phenyl Isothiocyanate → HCID 53927476, compound

HRID 1449608Notes

Reaction equation

HRID 1449608 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 (El, M.+) m/z 209. 1H-NMR (DMSO-d6 ; 400 MHz) δ9.88 (s, 1H), 7.70 (t, 1H), 7.52 (s, 1H), 7.47 (d, 2H), 7.31 (t, 2H), 7.15 (s, 1H), 7.09 (t, 1H), and 4.08 ppm (d, 2H).

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-439cf274ef654925911f0b941a7a5c25
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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