Water → HCID 86687762, compound

HRID 1473680Notes

Reaction equation

HRID 1473680 reaction equation
C([S:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][C:21]=3[O:28][CH3:29])=[N:14][C:15]([CH3:19])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC(O)=O.[OH2:34].[Cl:35]N1C(C)(C)C(=O)N(Cl)C1=O.[OH2:46]>C(Cl)Cl>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([C:13]2[C:12]3[C:17](=[CH:18][C:9]([S:8]([Cl:35])(=[O:46])=[O:34])=[CH:10][CH:11]=3)[N:16]=[C:15]([CH3:19])[N:14]=2)=[C:21]([O:28][CH3:29])[CH:22]=1)#[N:25]

Participants

6

Reactant 4

HCID 962WaterHCID 83601,3-Dichloro-5,5-dimethylhydantoinHCID 21899381Acetic acid--water (1/1)HCID 86687763HCID 86687763, compound

Product 1

HCID 86687762HCID 86687762, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(7-(benzylthio)-2-methylquinazolin-4-yl)-3-methoxybenzonitrile (0.371 g, 0.933 mmol) in 8 mL DCM and 0.2 mL (3:2 HOAc/water) solution was cooled to 0° C. and was treated with 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione (0.368 g, 1.867 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 (0-50% EtOAc/heptane) gave 4-(4-cyano-2-methoxyphenyl)-2-methylquinazoline-7-sulfonyl chloride (0.214 g, 0.572 mmol, 61.3% yield). (M+H)+=374.1.

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 (0-50% EtOAc/heptane)

Sources & evidence

ORD record
ord-b2b8d840867b47f38def5edfde509d5e
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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