Water → HCID 123300953, compound

HRID 1497701Notes

Reaction equation

HRID 1497701 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Li+].[CH3:24][Si]([N-][Si](C)(C)C)(C)C.CI.O>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[CH:9]([N:16]([CH3:24])[S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 131734225HCID 131734225, compound

Product 1

HCID 123300953HCID 123300953, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-Methyl-propane-2-sulfinic acid [(2-amino-5-bromo-phenyl)-phenyl-methyl]-amide (60 g, 157 mmol) in DMF (700 mL) is cooled to −20° C., then LiHMDS (163 mL, 173 mmol) is added dropwise. After the addition the mixture is stirred at −20° C. for 1 h. Then CH3I (22.3 g, 157 mmol) is added dropwise. After the addition the mixture is warm to r.t. for 2 h. Then H2O is added and is was extracted with MeO(CH3)3, dried over Na2SO4 and concentrated to give product.

Workup

  1. additionAfter the addition the mixture
  2. additionAfter the addition the mixture
  3. temperatureis warm to r.t. for 2 h
  4. extractionis was extracted with MeO(CH3)3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give product

Sources & evidence

ORD record
ord-481651abeffd4b0c9b3825e2265e48bf
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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