Propylamine → HCID 20208513, compound

HRID 542492Notes

Reaction equation

HRID 542492 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH:11][C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=[O:13].ClC(O[C:24](Cl)=[O:25])(Cl)Cl.[CH2:27]([NH2:30])[CH2:28][CH3:29]>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:24]([NH:30][CH2:27][CH2:28][CH3:29])=[O:25])=[CH:6][C:5]=1[NH:11][C:12]([NH:14][CH:15]([CH3:16])[CH3:17])=[O:13]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 10426DiphosgeneHCID 22152166HCID 22152166, compound

Product 1

HCID 20208513HCID 20208513, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A solution of methyl-4-amino-2-(3-isopropylureido)benzoate (500 mg), prepared as described in Preparation XVIII, above, in ethyl acetate (10 ml) was added to a solution of trichloromethylchloroformate (0.157 gm) in 5 ml ethyl acetate. After 11/2 hours, 5 ml of n-propylamine was added. The solution was diluted with ethyl acetate, extracted with water, 5% hydrochloric acid and washed with saturated sodium bicarbonate solution. The ethyl acetate layer was dried over magnesium sulphate and evaporated to yield methyl-4-(3-propylureido)-2-(3-isopropylureido)benzoate, as a solid, m.p. 94°-95° C.

Workup

  1. extractionextracted with water, 5% hydrochloric acid
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-184f62c93280459682bfbd57d0366d06
Source dataset
uspto-grants-1987_04
Patent number
US04657893

Reaction notes

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