Hydrochloric Acid → Benzo[1,3]dioxol-5-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide

HRID 619034

Reaction equation

HRID 619034 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH2:16])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3].[O:17]1[C:21]2[CH:22]=[CH:23][C:24]([S:26](Cl)(=[O:28])=[O:27])=[CH:25][C:20]=2[O:19][CH2:18]1.Cl>N1C=CC=CC=1>[N+:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:12]=[C:13]([NH:16][S:26]([C:24]3[CH:23]=[CH:22][C:21]4[O:17][CH2:18][O:19][C:20]=4[CH:25]=3)(=[O:27])=[O:28])[S:14][CH:15]=2)[CH:8]=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 49134011,3-Benzodioxole-5-sulfonyl chlorideHCID 218455864-(3-Nitrophenyl)thiazol-2-amine hydrochloride

Product 1

HCID 85768012Benzo[1,3]dioxol-5-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amideYield 38.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrochloride with 0.52 g of benzo[1,3]dioxol-5-sulfonyl chloride was stirred overnight with 2 ml of pyridine. The resulting, red colored suspension was poured into 25 ml of 1N hydrochloric acid and the solid which thereby separated was filtered off and dissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution. After the addition of 0.5 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 100 ml of 60% ethanol yielded 0.30 g of benzo[1,3]dioxol-5-sulfonic acid [4-(3-nitro-phenyl)-thiazol-2-yl]-amide as yellowish crystals.

Workup

  1. customthe solid which thereby separated
  2. filtrationwas filtered off
  3. dissolutiondissolved in a mixture of 30 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  4. additionAfter the addition of 0.5 g of active charcoal the mixture
  5. filtrationsubsequently the active charcoal was filtered off
  6. customThe product separated upon neutralization with concentrated hydrochloric acid
  7. customRecrystallization from 100 ml of 60% ethanol

Sources & evidence

ORD record
ord-587851bb37a14b05ab09067a6ad49a60
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Linked notes

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