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Methanesulfonyl chloride → HCID 12019007, compound

HRID 844316
Notes
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Reaction equation

HRID 844316 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[S:26])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=2)[CH:5]=[C:6]([Cl:12])[C:7]=1[O:8][CH2:9][CH2:10][OH:11].[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14](=[S:26])[NH:13][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH2:9][CH2:10][O:11][S:28]([CH3:27])(=[O:30])=[O:29])=[C:6]([Cl:12])[CH:5]=2)=[CH:17][CH:18]=1)(=[O:25])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15907988HCID 15907988, compound

Product 1

HCID 12019007HCID 12019007, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of N-(4-{3-[3,5-dichloro-4-(2-hydroxy-ethoxy)-phenyl]-thioureido}-phenyl)-acetamide (0.20 g) in pyridine (2 mL) and tetrahydrofuran (0.5 mL) is added methanesulfonyl chloride (0.11 g) and the solution is stirred at 0° C. for 45 minutes. The reaction mixture is then diluted with ethyl acetate, washed successively twice with 2% aqueous hydrochloric acid, once with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After removing the solvents by evaporation under reduced pressure the resulting residue is recrystallized from acetone-hexanes to give the desired product as a white powder.

Workup

  1. washwashed successively twice with 2% aqueous hydrochloric acid, once with saturated aqueous sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter removing the solvents
  4. customby evaporation under reduced pressure the resulting residue
  5. customis recrystallized from acetone-hexanes

Sources & evidence

ORD record
ord-8d7561823bd14c5f8a236da9a91093ba
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06380243B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes