Chloroform → HCID 178457878, compound

HRID 2240327Notes

Reaction equation

HRID 2240327 reaction equation
[CH2:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([SH:12])[S:11][C:7]=2[CH:6]=1)[CH2:2][CH3:3].C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].[Cl:24][C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[SH:12][C:10]1[S:11][C:7]2[CH:6]=[C:5]([N:4]([CH2:1][CH2:2][CH3:3])[C:25]([Cl:24])=[O:27])[CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 178456732HCID 178456732, compound

Product 1

HCID 178457878HCID 178457878, compoundYield 200.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250 ml three-neck, round bottomed flask were added 6-(propylamino)-1,3-benzothiazole-2-thiol (500 mg, 2.23 mmol), chloroform (100 ml), and saturated aqueous NaHCO3 (75 ml). The solution was stirred (mechanical stirrer) for 10 min at 0° C. (ice-bath) for 10 min. Stirring was stopped, and a solution of triphosgene (235 mg 0.80 mmol) in CH2Cl2 (2 ml) was added to the lower (organic) phase. Stirring was resumed for 40 min, then the layers were separated, and the aqueous phase was extracted 2× with chloroform. The combined organic fractions were dried (MgSO4), filtered, and concentrated to afford 0.46 g (72%) of the carbamoyl chloride as a waxy solid. IR (neat) 1737 cm−1 (C═O).

Workup

  1. stirringStirring
  2. stirringStirring
  3. waitwas resumed for 40 min
  4. customthe layers were separated
  5. extractionthe aqueous phase was extracted 2× with chloroform
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f56ee06ab50c42b69e3a5ed4a94bc64d
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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