Methanol → HCID 20264017, compound

HRID 223553Notes

Reaction equation

HRID 223553 reaction equation
NC(N)=[S:3].CO.Cl.[CH2:8]([O:15][C:16]1[C:17]([CH3:26])=[N:18][CH:19]=[C:20]([CH:24]=[CH2:25])[C:21]=1[CH2:22]Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O>[CH3:26][C:17]1[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:21]([CH2:22][SH:3])[C:20]([CH:24]=[CH2:25])=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 202639413-Benzyloxy-4-chloromethyl-2-methyl-5-vinylpyridine hydrochloride

Product 1

HCID 20264017HCID 20264017, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well stirred solution of 0.11 mole of thiourea in 250 ml. methanol, under N2 is added 0.1 mole of 3-benzyloxy-4-chloromethyl-2-methyl-5-vinylpyridine hydrochloride. The mixture is refluxed for 1 hour and then cooled. A solution of 0.4 mole of sodium hydroxide in 50 ml. of water is added, and the resulting mixture refluxed for 30 minutes. After concentration in vacuo the reaction mixture is taken up between benzene and water and enough acetic acid added to neutralize the mixture. The organic layer is separated, washed well with water, dried, and concentrated to give 2-methyl-3-benzyloxy-4-mercaptomethyl-5-vinylpyridine.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperaturecooled
  3. temperaturethe resulting mixture refluxed for 30 minutes
  4. concentrationAfter concentration in vacuo the reaction mixture
  5. additionadded
  6. customThe organic layer is separated
  7. washwashed well with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2f199ab6dba74aa7a52b5461e52b29eb
Source dataset
uspto-grants-1982_10
Patent number
US04355034

Reaction notes

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