Water → HCID 22397152, compound

HRID 411235Notes

Reaction equation

HRID 411235 reaction equation
[N:1]([O-])=O.[Na+].O.[NH2:6][C:7]1[S:8][CH:9]=[CH:10][C:11]=1[S:12]([CH2:15][C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:17])(=[O:14])=[O:13]>C(O)(=O)C>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][NH:18][C:16]([C:15]2[S:12](=[O:14])(=[O:13])[C:11]3[CH:10]=[CH:9][S:8][C:7]=3[NH:6][N:1]=2)=[O:17])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22397162HCID 22397162, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22397152HCID 22397152, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing sodium nitrite (0.06 g) and water (1 mL) is cooled to 0° C. before adding a solution of 2-((2-amino-3-thienyl)sulfonyl)-N-(4-chlorobenzyl)-acetamide (Preparation 54, 0.255 g) in hot acetic acid (10 mL) dropwise. The solution is warmed to room temperature and stirred for 30 minutes. The reactionmixture is poured into a beaker containing ice. The crude product is collected by filtration and dried under high vacuum to provide 0.18 g (66%) of the title compound as a brown solid. Physical characteristics: MS (ESI+) m/z 356 (M+H)+.

Workup

  1. temperatureThe solution is warmed to room temperature
  2. additionThe reactionmixture is poured into a beaker
  3. additioncontaining ice
  4. filtrationThe crude product is collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-ae60edba5c924c0eb27d1813a26021a9
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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