Dimethyl Sulfoxide → HCID 86656159, compound

HRID 1192465Notes

Reaction equation

HRID 1192465 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[C:17]2[N:18]=[C:19]([CH3:21])[S:20][C:16]=2[CH:15]=[CH:14][C:13]=1[CH2:22][OH:23].C(N(CC)CC)C>C(Cl)Cl>[Br:11][C:12]1[C:17]2[N:18]=[C:19]([CH3:21])[S:20][C:16]=2[CH:15]=[CH:14][C:13]=1[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67258380HCID 67258380, compound

Product 1

HCID 86656159HCID 86656159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethyl sulfoxide (1.13 mL, 0.016 mol) was added to oxalyl chloride (0.84 mL, 0.0099 mol) in methylene chloride (37.10 mL) at −78° C. After 10 minutes, (4-bromo-2-methyl-1,3-benzothiazol-5-yl)methanol (1.71 g, 0.00662 mol) in methylene chloride (74 mL) was added and the resultant mixture was stirred at −78° C. for 30 minutes. Triethylamine (4.62 mL, 0.0331 mol) was then added and the mixture was stirred for 5 h and the temperature allowed to gradually warm up to room temperature. After quenching with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated to dryness. The resultant solid was used directly in next step (1.70 g, 100%). LCMS calculated for C9H7BrNOS(M+H)+: m/z=255.9; found: 255.9.

Workup

  1. customAfter quenching with water
  2. extractionthe mixture was extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-7222bbc1490d478e9b68e461c1457b77
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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