Chloroform → HCID 54221449, compound

HRID 1939380Notes

Reaction equation

HRID 1939380 reaction equation
[O:1]([CH2:9][CH2:10][CH:11]1[C:16](=[O:17])[NH:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[O:12]1)[Si](C(C)(C)C)(C)C.[Cl:22][C:23]1[S:27][C:26]([CH2:28]Cl)=[CH:25][CH:24]=1.CCOC(C)=O.C(Cl)(Cl)Cl>CCCCCC.O>[Cl:22][C:23]1[S:27][C:26]([CH2:28][N:15]2[C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[O:12][CH:11]([CH2:10][CH2:9][OH:1])[C:16]2=[O:17])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 5830792-Chloro-5-(chloromethyl)thiopheneHCID 120480202-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 54221449HCID 54221449, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Prepared from 2-(2-tert-butyldimethylsiloxyethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazine by Methods F and G, alkylating with 5-chloro-2-(chloromethyl)thiophene and was isolated in 83% overall yield as a light yellow viscous oil after flash chromatography using 30-50% EtOAc in hexane; IR (CHCl3) 3418, 2943, 1677, 1500, 1400, 1278, 1062, 750 cm-1 ; 1H NMR (CDCl3) δ2.11-2.32 (m, 3H), 3.89 (q, J=5.4 Hz, 2H), 4.78 (dd, J=7.6, 5.5 Hz, 1H), 5.15 (ABq, JAB =16.0 Hz, 2H), 6.74 (d, J=3.7 Hz, 1H), 6.84 (d, J=3.7 Hz, 1H), 7.01-7.08 (m, 4H); MH+ at m/z=324; Anal. Calc'd for C15H14ClNO3S.0.25 H2O: C, 54.88; H, 4.45; N, 4.27; S, 9.77. Found: C, 54.86; H, 4.41; N, 4.04; S, 9.87.

Workup

  1. customwas isolated in 83%
  2. customoverall yield as a light yellow viscous oil after flash chromatography

Sources & evidence

ORD record
ord-a481915936d34cd2aa01b227b6376775
Source dataset
uspto-grants-1997_12
Patent number
US05696117

Reaction notes

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