Chlorosulfonic acid → HCID 86648024, compound

HRID 1666573Notes

Reaction equation

HRID 1666573 reaction equation
[CH3:1][C:2]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[I:18])=[N:7][N:6]=1)([CH3:4])[CH3:3].[Cl:20][S:21](O)(=[O:23])=[O:22]>>[CH3:4][C:2]([C:5]1[S:9][C:8]([NH:10][C:11]([C:12]2[CH:17]=[C:16]([S:21]([Cl:20])(=[O:23])=[O:22])[CH:15]=[CH:14][C:13]=2[I:18])=[O:19])=[N:7][N:6]=1)([CH3:1])[CH3:3]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 1087669HCID 1087669, compound

Product 1

HCID 86648024HCID 86648024, compound

Procedure

N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-2-iodobenzamide (600 mg) was added to 2 ml chlorosulfonic acid and heated at 180 C in a microwave for 1 min. The reaction was cooled to rt and added dropwise to ice water. A solid resulted, was filtered off, and was vacuum dried to give 450 mg of crude 3-({[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]amino}carbonyl)-4-iodobenzenesulfonyl chloride which was add to 5 ml of a 2M ethyl amine solution in THF. The reaction was stirred at it for 15 min and then washed with water and evaporated to give 280 mg crude product. 50 mg of this solid was purified by HPLC to give 36 mg N-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-5-[(ethylamino)sulfonyl]-2-iodobenzamide which was pure by LCMS.

Workup

  1. temperatureheated at 180 C in a microwave for 1 min
  2. customA solid resulted
  3. filtrationwas filtered off
  4. customdried

Sources & evidence

ORD record
ord-dff452d91db947f39a4a2565fa28bafc
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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