Water → HCID 67591300, compound

HRID 1290597Notes

Reaction equation

HRID 1290597 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5](=[N:24][C:25]1[CH:36]=[CH:35][C:28]([C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])=[CH:27][CH:26]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]23[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]4)[CH2:15]2)[CH2:21]3)[CH:7]=1.O>COCOC.COCCOC>[CH3:1][S:2][C:5](=[N:24][C:25]1[CH:36]=[CH:35][C:28]([C:29]([O:31][CH2:32][CH:33]=[CH2:34])=[O:30])=[CH:27][CH:26]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([C:14]23[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]4)[CH2:15]2)[CH2:21]3)[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 88303404HCID 88303404, compound

Product 1

HCID 67591300HCID 67591300, compound

Reagents, catalysts & solvents 2

HCID 8020DimethoxymethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a round bottom flask, 700 mg (10 mmoles) of sodium thiomethylate are suspended in 25 ml of dimethoxymethane. At ambient temperature and under a nitrogen stream, there are slowly introduced 3.5 g (7.6 mmoles) of allyl 4-[α-chloro-3-(1-adamantyl)-4-methoxybenzylideneamino]benzoate obtained in Example 4(b) and dissolved in 50 ml of DME. After 3 hours of reaction, the mixture is poured into water and extracted with ethyl ether. The organic phase is dried on sodium sulfate, then evaporated under a vacuum; the resulting crude product is chromatographed on a silica column eluted with a 20/80 mixture of ethyl ether and hexane. After evaporation of the solvents 2.6 g (73%) of the expected product whose melting point is 50°-53° C. are obtained.

Workup

  1. customAt ambient temperature
  2. customAfter 3 hours of reaction
  3. extractionextracted with ethyl ether
  4. customThe organic phase is dried on sodium sulfate
  5. customevaporated under a vacuum
  6. customthe resulting crude product is chromatographed on a silica column
  7. washeluted with a 20/80 mixture of ethyl ether and hexane
  8. customAfter evaporation of the solvents 2.6 g (73%) of the expected product whose melting point is 50°-53° C.
  9. customare obtained

Sources & evidence

ORD record
ord-7b7d11aa57354ea7b6987385a38ba65a
Source dataset
uspto-grants-1998_05
Patent number
US05753239

Reaction notes

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