Bromomethyl methyl ether → HCID 66717624, compound

HRID 2251316Notes

Reaction equation

HRID 2251316 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:19])(=[O:18])[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].[CH3:20][O:21][CH2:22]Br>ClCCl.C(N(CC)C(C)C)(C)C>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[S:10](=[O:19])(=[O:18])[N:11]([CH2:20][O:21][CH3:22])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4]

Participants

5

Reactant 2

HCID 83093Bromomethyl methyl etherHCID 3726134HCID 3726134, compound2×

Product 1

HCID 66717624HCID 66717624, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
0 °C

Procedure

The Sulfonamide of Step One, 3-phenylsulfamoylthiophene-2-carboxylic acid methyl ester, was dissolved in dry dichloromethane and N,N-diisopropyl ethylamine. The resulting mixture was chilled to 0° C. prior to the addition of bromomethyl methyl ether. The reaction mixture was stirred over night at room temperature. The mixture was partitioned between dichloromethane and aqueous HCl (2N). The organic layer will then be washed one time with saturated sodium chloride solution and dried over sodium sulfate, followed by concentration to dryness under reduced pressure to give the desired product, 3-(N-methoxymethyl-N-phenylsulfamoyl)thiophene-2-carboxylic acid methyl ester (3 g, quantitative).

Workup

  1. customThe mixture was partitioned between dichloromethane and aqueous HCl (2N)
  2. washThe organic layer will then be washed one time with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationfollowed by concentration to dryness under reduced pressure

Sources & evidence

ORD record
ord-5847ea4da0e14787b9f6f3e5db694f7d
Source dataset
uspto-grants-2008_01
Patent number
US07319111B2

Reaction notes

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