Water → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463077Notes

Reaction equation

HRID 463077 reaction equation
BrN1C(=[O:7])CCC1=O.[Cl:9][C:10]1[CH:11]=[C:12]([S:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]3[NH:31][C:30](=[O:32])[O:29][C:28]([CH3:34])([CH3:33])[C:27]=3[CH:35]=2)[CH:13]=[CH:14][C:15]=1[Cl:16].O>CO>[Cl:9][C:10]1[CH:11]=[C:12]([S:17]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]3[NH:31][C:30](=[O:32])[O:29][C:28]([CH3:33])([CH3:34])[C:27]=3[CH:35]=2)=[O:7])[CH:13]=[CH:14][C:15]=1[Cl:16]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 132540186-[4-(3,4-dichloro-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Product 1

HCID 132539416-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One gram (0.0056 mol) of N-bromosuccinimide is gradually added to a solution of 2.13 gm (0.005 mol) of 6-[4-(3,4-dichlorophenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one in 50 ml of methanol, under stirring. After reaction for 24 hours, 500 ml of water at 80° C. is added, and the precipitate is subjected to suction filtration after stirring for two hours. By recrystallization from isopropanol/diisopropylether, crystals are obtained, melting point: 136°-139° C.

Workup

  1. customAfter reaction for 24 hours
  2. filtrationthe precipitate is subjected to suction filtration
  3. stirringafter stirring for two hours
  4. customBy recrystallization from isopropanol/diisopropylether, crystals
  5. customare obtained

Sources & evidence

ORD record
ord-9077f9fdcd4347dba4c66cd491ce874b
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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