Hydrochloric Acid → 2-Amino-4-(4-aminophenylsulfonylmethyl)thiazole

HRID 1656940Notes

Reaction equation

HRID 1656940 reaction equation
C([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=1)(=O)C.Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15729146HCID 15729146, compound

Product 1

HCID 157291472-Amino-4-(4-aminophenylsulfonylmethyl)thiazoleYield 60.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-acetylamino-4-[4-aminophenylsulfonylmethyl)thiazole (4.8 g) in a mixture of acetic acid (35 ml) and 6N-aqueous hydrochloric acid (10 ml) was refluxed for 2.5 hours with stirring. The reaction mixture was poured into ice-water and then the solution was adjusted to pH 8.0 using 10% aqueous sodium bicarbonate with stirring. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-amino-4-(4-aminophenylsulfonylmethyl)thiazole (2.50 g, yield: 60.2%). mp: 203°-206° C. (dec.) IR (Nujol): 3450, 3350, 1630, 1595, 1530 1380 cm-1

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. stirringwith stirring
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-250c1042557d4ffcba2eb8af5873177f
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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