Chlorosulfonyl isocyanate → HCID 10039065, compound

HRID 2223359Notes

Reaction equation

HRID 2223359 reaction equation
ClS([N:5]=[C:6]=[O:7])(=O)=O.[NH2:8][C:9]1[S:10][C:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:13]=1[C:14]([NH2:16])=[O:15]>ClCCl>[CH2:17]([C:11]1[S:10][C:9]([NH:8][C:6]([NH2:5])=[O:7])=[C:13]([C:14]([NH2:16])=[O:15])[CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 38534572-amino-5-benzylthiophene-3-carboxamide

Product 1

HCID 10039065HCID 10039065, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chlorosulfonyl isocyanate (0.09 mL, 1.03 mmol) was added dropwise under nitrogen to a solution of 2-amino-5-benzyl-thiophene-3-carboxylic acid amide (0.2 g, 0.86 mmol) in dry dichloromethane (9 mL) at 0° C. and. The temperature of the resulting stirred reaction mixture was slowly raised from 0° C. to room temperature over 1 h. Once the LC-MS showed no starting material remaining, the reaction was quenched with water (1 mL) and stirred for 10 additional min. The solvent was removed under vacuum and the residue was taken up into DMSO (2 mL) and purified utilizing a Gilson preparative HPLC to give the above titled compound as a light brown solid (0.16 g, 67%). LC-MS [M+H]+ m/z 276.

Workup

  1. customreaction mixture
  2. temperaturewas slowly raised from 0° C. to room temperature over 1 h
  3. customthe reaction was quenched with water (1 mL)
  4. stirringstirred for 10 additional min
  5. customThe solvent was removed under vacuum
  6. custompurified

Sources & evidence

ORD record
ord-1331ab375b15477d9425a53a85c4aae2
Source dataset
uspto-grants-2008_05
Patent number
US07375131B2

Reaction notes

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