Ammonia → 5-Thiazolecarboxamide, 2-(2-methoxyphenyl)-4-methyl-

HRID 637708Notes

Reaction equation

HRID 637708 reaction equation
N.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]([C:16]([O:18]CC)=O)=[C:13]([CH3:15])[N:14]=1.COC1C=CC=CC=1C([NH2:27])=O.ClC(C(C)=O)C(OCC)=O.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>C(O)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]([C:16]([NH2:27])=[O:18])=[C:13]([CH3:15])[N:14]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 11858Ethyl 2-chloroacetoacetateHCID 14817Phosphorus sulfide (P2S5)HCID 755402-MethoxybenzamideHCID 13576837Ethyl 4-Methyl-2-(2-methoxyphenyl)thiazole-5-carboxylate

Product 1

HCID 30680725-Thiazolecarboxamide, 2-(2-methoxyphenyl)-4-methyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a solvent mixture of 50 ml of aqueous 28% ammonia and 450 ml of ethanol, 13.9 g of ethyl 2-(2-methoxyphenyl)-4-methylthiazole-5-carboxylate which had been prepared by heating a mixture of o-methoxybenzamide, ethyl α-chloroacetoacetate and phosphorus pentasulfide under a reflux condenser for 5 hours was dissolved. Then in a similar manner as in Example 3 the object was obtained as colourless minute aciculate melting at 191° to 192.5° C. in an amount of 8.7 g corresponding to the yield of 70%.

Workup

  1. customhad been prepared
  2. temperatureby heating
  3. dissolutionwas dissolved
  4. customThen in a similar manner as in Example 3 the object was obtained as colourless minute aciculate melting at 191° to 192.5° C. in an amount of 8.7 g corresponding to the yield of 70%

Sources & evidence

ORD record
ord-0e9fc0c8479b48fab0fa64aa08edf051
Source dataset
uspto-grants-1985_12
Patent number
US04558059

Reaction notes

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