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Methyl chloroformate → 12-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-5,10-dicarboxylic acid dimethyl ester

HRID 1393235
Notes
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Reaction equation

HRID 1393235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:19]3[CH2:20][NH:21][CH2:22][CH:12]2[C:13]2[CH:14]=[N:15][NH:16][C:17]=2[CH2:18]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:24]([O:26][CH3:27])=[O:25]>N1C=CC=CC=1.C(Cl)Cl>[CH3:27][O:26][C:24]([N:16]1[C:17]2[CH2:18][CH:19]3[N:11]([S:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)(=[O:9])=[O:10])[CH:12]([CH2:22][N:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20]3)[C:13]=2[CH:14]=[N:15]1)=[O:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 1604539412-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene

Product 1

HCID 5967948412-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-5,10-dicarboxylic acid dimethyl esterYield 100.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

12-(4-Chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene (204 mg, 0.602 mmol) was dissolved in pyridine (1 mL) and cooled to 0° C. Methyl chloroformate (0.139 mL, 1.80 mmol) was added over 15 minutes and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was diluted with methylene chloride (10 mL), washed with aqueous HCl (5 mL, 1 N) and aqueous NaHCO3 (5 mL), dried (Na2SO4), filtered and concentrated under vacuum to give 275 mg of 12-(4-chloro-benzenesulfonyl)-4,5,10,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-5,10-dicarboxylic acid dimethyl ester as a brown oil. Retention time (min)=1.704, method [1], MS(ESI) 455.1 (M+H).

Workup

  1. washwashed with aqueous HCl (5 mL, 1 N) and aqueous NaHCO3 (5 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b30ea042abe84bb18f11570ab39ad138
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07345056B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes