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Chlorosulfonyl isocyanate → Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate

HRID 1591837
Notes
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Reaction equation

HRID 1591837 reaction equation
[CH2:1]([S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)(=[O:5])=[O:4])[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O>O1CCCC1>[C:30]([C:15]1[N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C:13]([C:10]2[CH:9]=[CH:8][C:7]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:12][CH:11]=2)=[CH:17][CH:16]=1)#[N:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 69412284tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate

Product 1

HCID 16051190Tert-butyl 2-cyano-5-{4-{(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate (3.0 g, 8.58 mmol) was dissolved in tetrahydrofuran (85 mL) and cooled to −78° C., followed by the slow addition of chlorosulfonyl isocyanate. After tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed, dimethyl formamide (6.86 mL) was added and the solution allowed to warm to room temperature. After 2 hours, the mixture was cooled and partitioned between water and diethyl ether. The combined organic layers were dried over magnesium sulfate, and concentrated. The residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3) to afford the title compound (1.84 g, 57%). The title compound was used immediately in the next step.

Workup

  1. customAfter tert-Butyl 2-{4-[(ethylsulfonyl)amino]phenyl}-1H-pyrrole-1-carboxylate was consumed
  2. additiondimethyl formamide (6.86 mL) was added
  3. temperatureto warm to room temperature
  4. temperaturethe mixture was cooled
  5. custompartitioned between water and diethyl ether
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel flash chromatography (hexane/ethyl acetate; 7:3)

Sources & evidence

ORD record
ord-7fee40175bcb41cb9cc38f0cffe36a89
Source dataset
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07291643B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes