Acetic Acid → HCID 178479375, compound

HRID 1935319Notes

Reaction equation

HRID 1935319 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10](C(OC(C)(C)C)=O)[C:11]([NH2:20])=[N:12]C(OC(C)(C)C)=O)[CH:5]=1)([O-:3])=[O:2].B(Cl)(Cl)[Cl:29].C(O)CCC.C(O)(=O)C>C(Cl)Cl.O>[ClH:29].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([NH2:20])=[NH:12])[CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2631-ButanolHCID 25135Boron TrichlorideHCID 698717521-Nitro-3-(n,n'-bis(tert-butyloxycarbonyl)guanidino)benzene

Product 1

HCID 178479375HCID 178479375, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of compound 17 (238 milligrams, 0.492 millimoles) in CH2Cl2 was added 1.97 milliliters of 1 molar BCl3 (1.97 millimoles) in CH2Cl2. After 30 minutes, excess BCl3 and CH2Cl2 were removed by passing a stream of nitrogen gas across the surface of the solution. The resulting material was washed with CH2Cl2. The product was obtained as a white powder in 62% yield. TLC (4:1:1 n-butanol:acetic acid:water) indicated a single spot that was also UV active (Rf=0.47). 1H-NMR (DMSO): δ7.6-7.8 (m, 3H), 8.0-8.15 (m, 1H), 10.25 (brs.).

Workup

  1. customexcess BCl3 and CH2Cl2 were removed
  2. washThe resulting material was washed with CH2Cl2
  3. customThe product was obtained as a white powder in 62% yield

Sources & evidence

ORD record
ord-802cfeb82c674db3b9d5f33671f6eabe
Source dataset
uspto-grants-2002_05
Patent number
US06387890B1

Reaction notes

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