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Hydrochloric Acid → HCID 57439914, compound

HRID 906455
Notes
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Reaction equation

HRID 906455 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[S:13](Cl)(=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.Cl>C1COCC1.C(OCC)(=O)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[SH:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 574399006-Bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride

Product 1

HCID 57439914HCID 57439914, compoundYield 25.2%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-bromo-1-oxo-1,2-dihydroisoquinoline-4-sulfonyl chloride (Example 46a, 1 g) in THF (12 mL) was added triphenylphosphine (2.85 g). After 5 min, water (0.48 mL) was added followed by DMF (0.6 mL) and the reaction stirred for 1 h. Ethyl acetate and 2M HCl (aq) were added and the mixture shaken vigorously. The solid was filtered off and washed with further water and ethyl acetate before drying in vacuo at room temperature is for 2 h to afford the subtitle compound (0.2 g).

Workup

  1. stirringthe mixture shaken vigorously
  2. filtrationThe solid was filtered off
  3. washwashed with further water and ethyl acetate
  4. custombefore drying in vacuo at room temperature
  5. waitis for 2 h

Sources & evidence

ORD record
ord-fd6392823a4747a2bef17464c98e432a
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012980B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes