Allylamine → HCID 15053380, compound

HRID 2081482Notes

Reaction equation

HRID 2081482 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:12][N:11]([C:13](Cl)=[O:14])[CH2:10]2)=[CH:4][CH:3]=1.[CH2:16]([NH2:19])[CH:17]=[CH2:18]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:12][N:11]([C:13]([NH:19][CH2:16][CH:17]=[CH2:18])=[O:14])[CH2:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7853AllylamineHCID 150533761-Azetidinecarbonyl chloride, 3-[(4-chlorophenyl)thio]-

Product 1

HCID 15053380HCID 15053380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.6 g (0.01 mole) of 3-[(4-chlorophenyl)thio]-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was cooled in a water bath and treated with 2.2 g (0.02 mole) of 2-propenylamine. After stirring for 3 hr, the reaction mixture was diluted with 200 ml of water and the product separated as a yellow oil. The oil slowly solidified to yield a dull orange-red waxy material. After decanting the water and allowing the residue to air dry, the residue was triturated 5 times with boiling isopropyl ether and the decanted solutions upon cooling yielded 5 solid fractions, from white to pale beige color. The fractions were all consistent with the expected product by mass spectral analysis and TLC showed only a single product. All five fractions were combined to give 1.7 g (60.3%), m.p. 88°-89° C.

Workup

  1. customthe product separated as a yellow oil
  2. customto yield a dull orange-red waxy material
  3. customAfter decanting the water
  4. customdry
  5. customthe residue was triturated 5 times with boiling isopropyl ether
  6. temperaturethe decanted solutions upon cooling
  7. customyielded 5 solid fractions

Sources & evidence

ORD record
ord-ac7931754e944ab9b3047555686427b4
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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