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Water → HCID 86687747, compound

HRID 1473670
Notes
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Reaction equation

HRID 1473670 reaction equation
C([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([CH:26]([F:28])[F:27])=[CH:21][C:20]=3[O:29][CH3:30])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC(O)=O.[OH2:35].[Cl:36]N1C(C)(C)C(=O)N(Cl)C1=O.[OH2:47]>C(Cl)Cl>[F:27][CH:26]([F:28])[C:22]1[C:23]([F:25])=[CH:24][C:19]([C:13]2[C:12]3[C:17](=[CH:18][C:9]([S:8]([Cl:36])(=[O:47])=[O:35])=[CH:10][CH:11]=3)[N:16]=[CH:15][N:14]=2)=[C:20]([O:29][CH3:30])[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 21899381Acetic acid--water (1/1)HCID 86687748HCID 86687748, compound

Product 1

HCID 86687747HCID 86687747, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of 7-(benzylthio)-4-(4-(difluoromethyl)-5-fluoro-2-methoxyphenyl)quinazoline (0.966 g, 2.265 mmol) in 22 mL DCM and 0.44 mL (3:2 HOAc/water) solution was cooled to 0° C. and was treated with 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.893 g, 4.53 mmol). After stirring for 15 minutes, LC/MS showed mostly product, so the reaction mixture was diluted with water. The layers were separated, and the organics were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography gave 4-(4-(difluoromethyl)-5-fluoro-2-methoxyphenyl)quinazoline-7-sulfonyl chloride (0.634 g, 1.574 mmol, 69.5% yield) as a white solid. (M+H)+=402.9.

Workup

  1. customThe layers were separated
  2. dry with materialthe organics were dried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by silica gel column chromatography

Sources & evidence

ORD record
ord-571043fc451e45118832651cb16db2f5
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012443B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes