Dichloromethane → HCID 67531839, compound

HRID 1506808Notes

Reaction equation

HRID 1506808 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([N:10](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[N:7](C(OC(C)(C)C)=O)[C:6]=2[CH:32]=1.[Cl:33]CCl.[C:36]1(=[O:46])[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38](=[O:45])[O:37]1>CCOCC>[ClH:33].[NH2:10][C:8]1[NH:7][C:6]2[CH:32]=[C:2]([NH:1][C:38]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:44]=3[C:36]([OH:46])=[O:37])=[O:45])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6811Phthalic AnhydrideHCID 67531620HCID 67531620, compound

Product 1

HCID 67531839HCID 67531839, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 100 mL round-bottomed flask equipped with a magnetic stir bar was added tert-butyl 6-amino-2-(bis(tert-butoxycarbonyl)amino)-1H-benzo[d]imidazole-1-carboxylate (0.142 g, 0.317 mmol), dichoromethane (10 mL) and isobenzofuran-1,3-dione (0.047 g, 0.317 mmol). The stirring solution was allowed stir for 24 hours at room temperature. Volatiles were evaporated under reduced pressure. The resulting residue was dissolved up in a 1:1:2 mixture of concentrated HCl, H2O and THF (10 mL) and allowed to stir for seven hours with ventilation. Volatiles were then evaporated under reduced pressure. The resulting solid was rinsed thoroughly with ether providing the title compound (0.083 g, 81% yield) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 7.95 (d, 1H), δ 7.71 (m, 2H), δ 7.59 (m, 2H), δ 7.47 (m, 1H), δ 7.30 (t, 1H) ppm; 13C NMR (75 MHz, CD3OD) δ 170.1, 132.9, 130.9, 130.2, 128.6, 126.5, 123.4, 118.2, 117.8, 112.1 ppm; HRMS (ESI) Calcd for C15H12N4O2 (M+) 296.0909. Found 296.0915.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with a magnetic stir bar
  2. customVolatiles were evaporated under reduced pressure
  3. dissolutionThe resulting residue was dissolved up in a 1:1:2 mixture of concentrated HCl, H2O and THF (10 mL)
  4. stirringto stir for seven hours with ventilation
  5. customVolatiles were then evaporated under reduced pressure

Sources & evidence

ORD record
ord-78723b0702ac40a88b4871437da181e4
Source dataset
uspto-grants-2015_12
Patent number
US09221765B2

Reaction notes

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