Benzoic acid, 3-isothiocyanato- → 1-Amino-3-(3-carboxyphenyl)-2-thioxoimidazolidin-4-one

HRID 555624

Reaction equation

HRID 555624 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])=[C:2]=[S:3].C(N(C(C)C)CC)(C)C.Cl.[NH:23]([CH2:25][C:26](OCC)=[O:27])[NH2:24]>ClCCl>[NH2:24][N:23]1[CH2:25][C:26](=[O:27])[N:1]([C:4]2[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=2)[C:2]1=[S:3]

Participants

5

Reactant 3

HCID 75046Benzoic acid, 3-isothiocyanato-HCID 81531DiisopropylethylamineHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 227309861-Amino-3-(3-carboxyphenyl)-2-thioxoimidazolidin-4-oneYield 22.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

179 mg (1 mmol) of 3-isothiocyanatobenzoic acid and 523 μl (3 mmol) of diisopropylethylamine were stirred in 8 ml of dichloromethane and then with 155 mg (1 mmol) of ethyl hydrazinoacetate hydrochloride at room temperature for 96 hours. After the solvent was concentrated, the mixture was partitioned between ethyl acetate and 30% acetic acid. The aqueous layer was extracted with ethyl acetate again, and the organic layers were combined, washed with water and then with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated. The resulting solid was mixed with a 190:10:0.8 liquid mixture of ethyl acetate, methanol and acetic acid, and the insoluble was dried to obtain 55.7 mg of the desired product (yield 22%).

Workup

  1. concentrationAfter the solvent was concentrated
  2. customthe mixture was partitioned between ethyl acetate and 30% acetic acid
  3. extractionThe aqueous layer was extracted with ethyl acetate again
  4. washwashed with water
  5. dry with materialwith saturated aqueous sodium chloride, dried over magnesium sulfate
  6. concentrationconcentrated
  7. additionThe resulting solid was mixed with a 190:10:0.8 liquid mixture of ethyl acetate, methanol and acetic acid
  8. customthe insoluble was dried

Sources & evidence

ORD record
ord-018a07c900464e40a116b11f3e1f83b6
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Linked notes

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