Water → HCID 86687756, compound

HRID 1473676Notes

Reaction equation

HRID 1473676 reaction equation
C([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([F:28])[F:27])=[CH:22][C:21]=3[O:29][CH3:30])=[N:14][C:15]([CH3:19])=[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:23]1[CH:24]=[CH:25][C:20]([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]=[C:15]([CH3:19])[N:14]=2)=[C:21]([O:29][CH3:30])[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 21899381Acetic acid--water (1/1)HCID 86687757HCID 86687757, compound

Product 1

HCID 86687756HCID 86687756, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(benzylthio)-4-(4-(difluoromethyl)-2-methoxyphenyl)-2-methylquinazoline (0.380 g, 0.899 mmol) in 11 mL DCM and 0.22 mL (3:2 HOAc/water) solution was cooled to 0° C. and was treated with 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.354 g, 1.799 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)-2-methoxyphenyl)-2-methylquinazoline-7-sulfonyl chloride (0.180 g, 0.451 mmol, 50.2% yield) as a white solid. (M+H)+=399.0.

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-0876cc1d45134f18947c46a28b34dd28
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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