Water → HCID 22000329, compound

HRID 618503

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]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 83783Phenol, 4-amino-, 1-acetateHCID 131721374HCID 131721374, compound

Product 1

HCID 22000329HCID 22000329, compound

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
Patent number
US05952382

Linked notes

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