Sodium Hydroxide → 2-Thiazolamine, 4-(3-aminophenyl)-N-methyl-

HRID 255899Notes

Reaction equation

HRID 255899 reaction equation
Br.[CH3:2][NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[CH:10]=[C:11]([NH:15]C(=O)OCC)[CH:12]=[CH:13][CH:14]=2)[N:8]=1.[OH-].[Na+]>Cl>[CH3:2][NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=2)[N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20165159HCID 20165159, compound

Product 1

HCID 14807842-Thiazolamine, 4-(3-aminophenyl)-N-methyl-Yield 86%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of ethyl N-[3-(2-methylamino-4-thiazolyl)-phenyl]-carbamate hydrobromide (33.5 g) and 10% hydrochloric acid (500 ml) was refluxed for 48 hours. After cooling, the solution was made alkaline with 10% sodium hydroxide and the precipitate was filtered off, washed with water and dried to give 16.5 g of 2-methylamino-4-(3-amino-phenyl)-thiazole; M.p. 118°-121° C. 2-Methylamino-4-(4-amino-phenyl)-thiazole; M.p. 178°-180° C., was prepared in analogous manner, starting from the appropriate carbamate derivative.

Workup

  1. temperaturewas refluxed for 48 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-037050a25b1942b2a696e57c4d8c6b02
Source dataset
uspto-grants-1987_10
Patent number
US04699915

Reaction notes

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