2-Morpholinoethylamine → HCID 21543975, compound

HRID 1606613Notes

Reaction equation

HRID 1606613 reaction equation
C(NC(=O)/C=C(\O[C:11](=[O:30])[C:12]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[C:15]([Cl:22])=[CH:14][C:13]=1[NH:23][CH2:24][C:25]1[O:29][CH:28]=[CH:27][CH:26]=1)/C)(C)(C)C.[NH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(#N)C>[O:38]1[CH2:39][CH2:40][N:35]([CH2:34][CH2:33][NH:32][C:11](=[O:30])[C:12]2[CH:17]=[C:16]([S:18]([CH3:21])(=[O:19])=[O:20])[C:15]([Cl:22])=[CH:14][C:13]=2[NH:23][CH2:24][C:25]2[O:29][CH:28]=[CH:27][CH:26]=2)[CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 21543983HCID 21543983, compound

Product 1

HCID 21543975HCID 21543975, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-tert-butyl-3-(2-furfurylamino-4-chloro-5-methylsulfonylbenzoyloxy)crotonamide (4.00 g.; 0.0085 mole) and N-(2-aminoethyl)morpholine (2.21 g.; 0.017 mole) are added to acetonitrile (100 ml.). The resulting solution is stirred at room temperature for 24 hours. The acetonitrile is removed under reduced pressure, and the residue is triturated with butyl chloride to give N-(2-morpholinoethyl)-2-furfurylamino-4-chloro-5-methylsulfonylbenzamide which after drying yields 2.7 g. (72%), m.p. 127°-130° C. Several recrystallizations from butyl chloride yields product with m.p. 132°-134° C.

Workup

  1. customThe acetonitrile is removed under reduced pressure
  2. customthe residue is triturated with butyl chloride

Sources & evidence

ORD record
ord-34d0616702dc47bfbeb68e918218bf13
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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