3,5-Diamino-2-methylbenzoic acid → HCID 178441517, compound

HRID 274325Notes

Reaction equation

HRID 274325 reaction equation
Cl.[C:2](=N)(OCC)[CH2:3][CH2:4][CH2:5][CH3:6].[NH2:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[NH2:22])[C:15]([O:17][CH3:18])=[O:16]>O1CCCC1>[CH2:3]([C:2]1[NH:22][C:21]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=2[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 1355243,5-Diamino-2-methylbenzoic acidHCID 12283341Ethyl pentanimidate hydrochloride

Product 1

HCID 178441517HCID 178441517, compoundYield 128.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

5.47 g of ethyl pentanimidoate hydrochloride (J.A.C.S., Vol. 64, p. 1827 (1942)) were added to a solution of 5 g of methyl 3,4-diaminobenzoate in 60 ml of tetrahydrofuran, and the mixture was stirred for 3 hours and 30 minutes at 90° C. The tetrahydrofuran was evaporated off and 50 ml of a saturated solution of sodium bicarbonate were added. The mixture was extracted with methylene chloride and the extracts were washed with water, dried and evaporated to dryness under reduced pressure to obtain 9 g of product which was crystallized from isopropyl ether to obtain 6.65 g of the desired product melting at 114° C.

Workup

  1. customThe tetrahydrofuran was evaporated off
  2. addition50 ml of a saturated solution of sodium bicarbonate were added
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe extracts were washed with water
  5. customdried
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-88288d5eed7847c2ad5bf0b88b9d4da0
Source dataset
uspto-grants-1995_02
Patent number
US05389634

Reaction notes

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