Ammonia → 5-Methyl-2-(3-pyridyl)-thiazole

HRID 1600452Notes

Reaction equation

HRID 1600452 reaction equation
[C:1]([CH2:4][NH:5][C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1)(=O)[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15].N.C>C1(C)C=CC=CC=1>[CH3:2][C:1]1[S:15][C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 297MethaneHCID 14817Phosphorus sulfide (P2S5)HCID 19612493N-Acetylmethyl-nicotinamide

Product 1

HCID 196125135-Methyl-2-(3-pyridyl)-thiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 8.0 g (0.045 mol) of 73 in 125 ml of toluene, 10 g (0.045 mol) of P4S10 was added. The suspension was refluxed for 4 h and left at room temperature overnight. The mixture was poured into ice water followed by basification with ammonia. The two-phase system was stirred with charcoal and filtered. The toluene phase was separated and the aqueous phase extracted with 2×100 ml of toluene. The combined organic phase were dried over MgSO4 and evaporated in vacuo leaving a heavy, yellow oil, 88. Yield: 2.3 g (0.013 mol), 29%).

Workup

  1. temperatureThe suspension was refluxed for 4 h
  2. filtrationfiltered
  3. customThe toluene phase was separated
  4. extractionthe aqueous phase extracted with 2×100 ml of toluene
  5. dry with materialThe combined organic phase were dried over MgSO4
  6. customevaporated in vacuo
  7. customleaving a heavy, yellow oil, 88

Sources & evidence

ORD record
ord-dddecb71856e4b40b10c34c0a9991333
Source dataset
uspto-grants-1999_11
Patent number
USRE036374

Reaction notes

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