Sodium Carbonate → HCID 21505609, compound

HRID 1287643Notes

Reaction equation

HRID 1287643 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[S:19][CH:20]=[C:21]([CH3:23])[N:22]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[Cr](O)(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH3:23][C:21]1[N:22]=[C:18]([C:15]2[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[O:24])[CH2:13][CH:14]=2)[S:19][CH:20]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24425Chromic AcidHCID 21505598HCID 21505598, compound

Product 1

HCID 21505609HCID 21505609, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A 1.4 g. portion of 3,6-dihydro-α-(p-fluorophenyl)- 4-(4-methyl-2-thiazolyl)-1(2H)-pyridinebutanol, prepared as described in Example 12, in 30 ml. of acetic acid is stirred at room temperature. A 24 ml. portion of chromic acid in acetic acid is added dropwise. The mixture is stirred for 3 hours and then allowed to stand overnight. The mixture is poured onto ice water and neutralized with sodium carbonate. The mixture is extracted 3 times with ether. The extracts are dried over magnesium sulfate, filtered and evaporated, giving an oil which solidifies. This solid is recrystallized twice from aqueous methanol yielding a tan solid, m.p. 81°-82° C.

Workup

  1. waitto stand overnight
  2. extractionThe mixture is extracted 3 times with ether
  3. dry with materialThe extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customgiving an oil which
  7. customThis solid is recrystallized twice from aqueous methanol yielding a tan solid, m.p. 81°-82° C.

Sources & evidence

ORD record
ord-3252f2f6762248aa8efe6849c91e55b7
Source dataset
uspto-grants-1976_10
Patent number
US03985754

Reaction notes

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