Phenoxyacetyl chloride → HCID 57585096, compound

HRID 2077581Notes

Reaction equation

HRID 2077581 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].[O:21]([CH2:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:29](=[O:30])[CH2:28][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 69703Phenoxyacetyl chloride2×HCID 57584985HCID 57584985, compound

Product 1

HCID 57585096HCID 57585096, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (100 mg, 328 μmol) in pyridine (0.3 mL) and DCM (2 mL) was added 2-phenoxyacetyl chloride (150 μl, 1086 μmol). A clear solution formed. More 2-phenoxyacetyl chloride (150 μl, 1086 μmol) was added until the reaction was complete. The DCM was evaporated and the mixture was diluted with EtOAc (10 mL). The mixture was filtered, washed with EtOAc, H2O (3×5 mL) and dried in air to give a gray powder. MS (ESI, POS. ION) M/Z: calc'd for C22H19ClN4O2S: 438.1. found: 439.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.85 (s, 6H) 4.95 (s, 2H) 6.90-7.08 (m, 3H) 7.33 (t, J=7.78 Hz, 2H) 7.75-7.92 (m, 3H) 8.36 (s, 1H) 8.44 (s, 1H) 12.70 (s, 1H).

Workup

  1. customA clear solution formed
  2. customThe DCM was evaporated
  3. additionthe mixture was diluted with EtOAc (10 mL)
  4. filtrationThe mixture was filtered
  5. washwashed with EtOAc, H2O (3×5 mL)
  6. customdried in air
  7. customto give a gray powder

Sources & evidence

ORD record
ord-28cddca0f44c49be85e18291f3daadec
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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