Chlorosulfonyl isocyanate → HCID 58234960, compound

HRID 1919356Notes

Reaction equation

HRID 1919356 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].ClS([N:24]=[C:25]=[O:26])(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[N:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:25]([NH2:24])=[O:26])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 58234965HCID 58234965, compound

Product 1

HCID 58234960HCID 58234960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzylamino-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.40 g, 1.45 mmol) in DCM (10 mL) was added chlorosulfonyl isocyanate (140 μL, 1.59 mmol) dropwise at −78° C. The mixture was allowed to warm to RT and stirred for 30 minutes. The resulting solution was concentrated in vacuo then dissolved in acetone (5 mL), before H2O (2 mL) was added dropwise. The mixture was stirred at RT for 30 minutes, then concentrated in vacuo. The resultant oil was partitioned between EtOAc and H2O. The organic layer was isolated, washed with brine, dried (MgSO4) and concentrated in vacuo to give 4-(1-benzyl-ureido)-2-methyl-thiazole-5-carboxylic acid ethyl ester as a pale brown oil. To a solution of 4-(1-benzyl-ureido)-2-methyl-thiazole-5-carboxylic acid ethyl ester in MeOH (10 mL) was added a solution of sodium methoxide in MeOH (25% w/w, 1.33 mL, 5.80 mmol) and the mixture was stirred at RT for 18 h. The crude reaction mixture was concentrated in vacuo and partitioned between EtOAc and an aqueous solution of HCl (1 M). The organic layer was isolated, washed with brine, then dried (MgSO4) and concentrated in vacuo. The resultant residue was triturated with EtOAc to give the title compound as a pale yellow solid (0.25 g, 63%).

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. dissolutionthen dissolved in acetone (5 mL), before H2O (2 mL)
  3. additionwas added dropwise
  4. stirringThe mixture was stirred at RT for 30 minutes
  5. concentrationconcentrated in vacuo
  6. customThe resultant oil was partitioned between EtOAc and H2O
  7. customThe organic layer was isolated
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ed26a60f6204cb587d9326d4b8e1d11
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

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