Prop-2-en-1-yl 4-aminobenzoate → Allyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate

HRID 1290599Notes

Reaction equation

HRID 1290599 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:21][C:22]1[CH:33]=[CH:32][C:25]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[CH:24][CH:23]=1>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=3[O:19][CH3:20])[CH:14]=[N:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:29][CH:30]=[CH2:31])=[O:27])=[CH:32][CH:33]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

3

Reactant 2

HCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 540295304-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylbenzaldehyde

Product 1

HCID 67591433Allyl 4-[3-(1-adamantyl)-4-methoxybenzylideneamino]benzoateYield 76%

Procedure

Starting with 3.4 g (12.6 mmoles) of 3-(1-adamantyl)-4-methoxybenzaldehyde and 2.6 g (14.4 mmoles) of allyl 4-aminobenzoate the synthesis is effected following the procedures described in Example 8. The resulting crude product is recrystallized in ethyl acetate. After filtration and drying, 4.1 g (76%) of the allylic ester whose melting point is 160°-162° C. are obtained.

Workup

  1. customThe resulting crude product is recrystallized in ethyl acetate
  2. filtrationAfter filtration
  3. customdrying

Sources & evidence

ORD record
ord-93190d88986149d38a252f0d0cafb641
Source dataset
uspto-grants-1998_05
Patent number
US05753239

Reaction notes

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