Hydrochloric Acid → 4-cyclohexyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 1417261

Reaction equation

HRID 1417261 reaction equation
Br.[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].[CH:17]1([C:23]2[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.Cl>N1C=CC=CC=1>[CH:17]1([C:23]2[CH:24]=[CH:25][C:26]([S:29]([NH:16][C:13]3[S:14][CH:15]=[C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=4)[N:12]=3)(=[O:31])=[O:30])=[CH:27][CH:28]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 28704454-(3-Nitro-phenyl)-thiazol-2-ylamine hydrobromideHCID 43394424-Cyclohexylbenzene-1-sulfonyl chloride

Product 1

HCID 218455904-cyclohexyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamideYield 20.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.5 g of 4-(3-nitro-phenyl)-thiazol-2-ylamine hydrobromide with 0.46 g of 4-cyclohexyl-benzenesulfonyl 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 organic phase was separated and dissolved in a mixture of 20 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 as an oil upon neutralization. Thereupon, 20 ml of ethanol were added, the mixture was boiled and insoluble material was filtered off. Crystals separated upon cooling and, after recrystallization from 40 ml of 50% ethanol, yielded 0.15 g of 4-cyclohexyl-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as beige crystals.

Workup

  1. customthe organic phase was separated
  2. dissolutiondissolved in a mixture of 20 ml of ethanol and 20 ml of 2N sodium hydroxide solution
  3. additionAfter the addition of 0.5 g of active charcoal the mixture
  4. filtrationsubsequently the active charcoal was filtered off
  5. customThe product separated as an oil upon neutralization
  6. additionThereupon, 20 ml of ethanol were added
  7. filtrationinsoluble material was filtered off
  8. customCrystals separated
  9. temperatureupon cooling
  10. customafter recrystallization from 40 ml of 50% ethanol

Sources & evidence

ORD record
ord-e11c64d403a34430830724b41f85273d
Source dataset
uspto-grants-1999_03
Patent number
US05877193

Linked notes

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