Water → 3-Acetamido-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)indol-2-one

HRID 234506Notes

Reaction equation

HRID 234506 reaction equation
[NH2:1][C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[O:24][CH3:25])(=[O:14])=[O:13])[C:3]1=[O:26].[C:34](Cl)(=[O:36])[CH3:35].O>N1C=CC=CC=1>[C:34]([NH:1][C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[O:24][CH3:25])(=[O:13])=[O:14])[C:3]1=[O:26])(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 190765153-Amino-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)indol-2-one

Product 1

HCID 190764193-Acetamido-5-chloro-3-(2-chlorophenyl)-1,3-dihydro-1-(2-methoxy-4-nitrobenzenesulfonyl)indol-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.8 g of the compound obtained in EXAMPLE 16 in 10 ml of pyridine is cooled in an ice bath and 0.51 ml of acetyl chloride is added. The reaction medium is stirred for 3 hours at RT and poured into water. It is extracted with AcOEt, washed with water and with a 5% solution of potassium hydrogensulfate, dried over sodium sulfate and evaporated under vacuum. The residue is taken up with DCM and the precipitate formed is filtered off to give 2.8 g of the expected product, a sample of which is crystallized from an MeOH/iso ether mixture. M.p.=205°-210° C.

Workup

  1. extractionIt is extracted with AcOEt
  2. washwashed with water and with a 5% solution of potassium hydrogensulfate
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customthe precipitate formed
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-c19adfc1efb543df87616ef1142563ef
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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