Phenoxyacetyl chloride → HCID 178521400, compound

HRID 2240326Notes

Reaction equation

HRID 2240326 reaction equation
[C:1]1([CH2:7][NH:8][C:9]2[CH:18]=[CH:17][C:12]3[N:13]=[C:14]([SH:16])[S:15][C:11]=3[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:19]([CH2:26][C:27](Cl)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[SH:16][C:14]1[S:15][C:11]2[CH:10]=[C:9]([N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:27](=[O:28])[CH2:26][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:18]=[CH:17][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 69703Phenoxyacetyl chlorideHCID 178527802HCID 178527802, compound

Product 1

HCID 178521400HCID 178521400, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 13×100 mm screw cap Pyrex® vial were added 6-[(phenylmethyl)amino]-1,3-benzothiazole-2-thiol (30.6 mg, 0.11 mmol), poly(vinylpyridine) (25 mg, 0.22 mmol), phenoxyacetyl chloride (25 μl, 0.18 mmol), and THF (2 ml). The vial was purged with Ar, capped, and shaken for 24 h. Amino silica gel (200 mg, 166 mmol) was added, and the suspension was shaken an additional 6 h. The suspension was filtered, and purified by preparative TLC (developing with 35% EtOAc in hexanes) to afford the title compound as a white powder (33.8 mg, 76%); 1H NMR (DMSO-d6) δ=4.48 (s, 2H), 4.83 (s, 2H), 6.73 (d, 2H), 6.88 (t, 1H), 7.27-7.15 (m, 9H), 7.57 (s, 1H); ESIMS: m/z 405 (M−H).

Workup

  1. customInto a 13×100 mm screw cap Pyrex®
  2. customThe vial was purged with Ar
  3. customcapped
  4. stirringthe suspension was shaken an additional 6 h
  5. filtrationThe suspension was filtered
  6. custompurified by preparative TLC (developing with 35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b2601ece864f47659a06ece16f5b97c6
Source dataset
uspto-grants-2010_05
Patent number
US07723366B2

Reaction notes

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