Water → HCID 11292384, compound

HRID 1435704Notes

Reaction equation

HRID 1435704 reaction equation
[Cl:1][C:2]1[C:3]([CH3:20])=[C:4]([S:8]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH2:17][CH2:18]O)[N:16]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:41].O>CN(C=O)C>[Br:41][CH2:18][CH2:17][C:15]1[N:16]=[C:12]([NH:11][S:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[CH3:20])(=[O:10])=[O:9])[S:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 87545745HCID 87545745, compound

Product 1

HCID 11292384HCID 11292384, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An ice-cold mixture of EXAMPLE 181A (2.03 g, 6.10 mmol), triphenylphosphine (4.80 g, 18.31 mmol) and carbontetrabromide (6.07 g, 18.31 mmol) in DMF (30 mL) was stirred for 1.5 h, and was then poured into water. The mixture was extracted with DCM, dried (sodium sulfate) and the solvent was evaporated. The crude material was twice purified by flash chromatography on silica gel gradient eluting with 0-4% acetone in DCM giving N-[4-(2-bromoethyl)-1,3-thiazol-2-yl]-3-chloro-2-methylbenzenesulfonamide as a solid (990 mg, 41%). MS (Ionspray, [M+H]+) m/z 394; Anal. Calcd. (found) for C12H12BrClN2O2S2: C, 36.4 (36.6)%; H, 3.1 (3.3)%; N ,7.1 (7.2)%.

Workup

  1. extractionThe mixture was extracted with DCM
  2. dry with materialdried (sodium sulfate)
  3. customthe solvent was evaporated
  4. customThe crude material was twice purified by flash chromatography on silica gel gradient
  5. washeluting with 0-4% acetone in DCM

Sources & evidence

ORD record
ord-1d98029a42734a5c8f27d666f9f1071f
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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