Carbon Dioxide → HCID 22155484, compound

HRID 1110375Notes

Reaction equation

HRID 1110375 reaction equation
B(Br)(Br)Br.[CH3:5][NH:6][S:7]([C:10]1[S:11][C:12]2[CH:18]=[C:17]([O:19]CC)[CH:16]=[CH:15][C:13]=2[N:14]=1)(=[O:9])=[O:8].C(=O)=O>C(Cl)Cl>[OH:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([S:7]([NH:6][CH3:5])(=[O:8])=[O:9])[S:11][C:12]=2[CH:18]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 25134Boron tribromideHCID 232746756-Ethoxy-N-methyl-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 22155484HCID 22155484, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A one molar solution of boron tribromide in CH2Cl2 (21 mL) was cooled to -76° C. in a dry ice/acetone bath. N-Methyl-6-ethoxy-2-benzothiazole-sulfonamide (1, og.; 0.0037 mol) was added and the reaction stirred in the dry ice bath for four hours. The reaction was removed, stirred at room temperature for 18 hours, poured into a mixture of 25 mL of crushed ice/25 mL water and stirred for 30 minutes. The crude material was collected and purified by dissolving in 10% Na2CO3, filtered, anc precipitated with dilute acetic acid (1:1) to give 0.75g (83.0% yield) of pure product, m.p. 189°-190° C.; NMR(DMSO-d ) delta 8.5-8.0(m, 3H); 7.6(d, lH); 7.4-7.2 (q, lH).

Workup

  1. customThe reaction was removed
  2. additionpoured into a mixture of 25 mL of crushed ice/25 mL water
  3. stirringstirred for 30 minutes
  4. customThe crude material was collected
  5. custompurified
  6. dissolutionby dissolving in 10% Na2CO3
  7. filtrationfiltered
  8. customanc precipitated with dilute acetic acid (1:1)

Sources & evidence

ORD record
ord-09de840ece6547e4a9c489f8ac7085ea
Source dataset
uspto-grants-1990_12
Patent number
US04975449

Reaction notes

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