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Water → N-(4-acetoxyphenyl)-4-[7-(1-adamantyl)-6-methoxy-ethoxymethoxy-2-naphthyl]benzamide

HRID 618503
Notes
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Reaction equation

HRID 618503 reaction equation
[C:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N([CH2:17][CH3:18])CC)C.[C:19]12([C:29]3[CH:38]=[C:37]4[C:32]([CH:33]=[CH:34][C:35]([C:41]5[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=5)=[C:36]4[O:39][CH3:40])=[CH:31][C:30]=3[O:50][CH2:51]COC)[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.[OH2:55]>C1COCC1>[C:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH:9][C:45](=[O:46])[C:44]2[CH:48]=[CH:49][C:41]([C:35]3[CH:34]=[CH:33][C:32]4[C:37](=[CH:38][C:29]([C:19]56[CH2:26][CH:25]7[CH2:24][CH:23]([CH2:22][CH:21]([CH2:27]7)[CH2:20]5)[CH2:28]6)=[C:30]([O:50][CH3:51])[CH:31]=4)[C:36]=3[O:39][CH2:40][O:55][CH2:17][CH3:18])=[CH:42][CH:43]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 83783Phenol, 4-amino-, 1-acetateHCID 1317213744-[7-(1-Adamantyl)-6-methoxyethoxy-methoxy-2-naphthyl]benzoic acid chloride

Product 1

HCID 22000329N-(4-acetoxyphenyl)-4-[7-(1-adamantyl)-6-methoxy-ethoxymethoxy-2-naphthyl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

970 mg (6.4 mmol) of 4-acetoxyaniline, 50 ml of THF and 990 μl (7 mmol) of triethylamine were introduced into a round-bottomed flask. A solution of 3.2 g (6.4 mmol) of 4-[7-(1-adamantyl)-6-methoxyethoxy-methoxy-2-naphthyl]benzoic acid chloride in THF was added dropwise and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was poured into water and extracted with ethyl acetate and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane, filtered and dried. 3.15 g (81%) of the expected compound were collected, which compound had a melting point of 206°-7° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated in heptane
  7. filtrationfiltered
  8. customdried
  9. custom3.15 g (81%) of the expected compound were collected

Sources & evidence

ORD record
ord-4ab03eda088a46eab3e2f958a65f9208
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05952382

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes