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Carbon Dioxide → HCID 15411537, compound

HRID 1075378
Notes
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Reaction equation

HRID 1075378 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]2[N:17]=[CH:18][S:19][C:15]=2[CH:14]=1.C(=O)=O.[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30][O:31][C:32]1[CH:42]=[CH:41][C:35]([C:36](OCC)=[O:37])=[CH:34][CH:33]=1.[NH4+].[Cl-]>CCCCCC.O1CCCC1.CC(C)=O>[CH3:6][O:7][CH2:8][CH2:9][O:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]2[N:17]=[C:18]([C:36](=[O:37])[C:35]3[CH:34]=[CH:33][C:32]([O:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH3:25])=[CH:42][CH:41]=3)[S:19][C:15]=2[CH:14]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 280Carbon Dioxide2×HCID 25517Ammonium ChlorideHCID 54038012Ethyl 4-[(2-methoxyethoxy)methoxy]benzoateHCID 545731596-[(2-Methoxyethoxy)methoxy]benzothiazoleHCID 178418339Butyllithium

Product 1

HCID 15411537HCID 15411537, compound
Yield 77.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1.3 N of n-butyllithium in hexane (0.7 ml) was added to a solution of 220 mg of 6-[(2-methoxyethoxy)methoxy]benzothiazole (obtained as in paragraph 1 above) in 30 ml of tetrahydrofuran at -78° C. cooled by dry ice--acetone. The mixture was added dropwise into a solution of 234 mg of ethyl 4-[(2-methoxyethoxy)methoxy]benzoate (obtained as in paragraph 2 above) in tetrahydrofuran (3 ml) cooled by dry ice--acetone. NH4Cl was added to the reaction mixture and the mixture was extracted with ether. The extracts were washed with water and dried over sodium sulfate. After being concentrated, the residue was recrystallized from ethyl acetate to yield 320 mg of 6-(2-methoxyethoxy)methoxy-2-{4-[(2-methoxyethoxy)methoxy]benzoyl}benzothiazole (Compound 1). mp: 46° C. 1H-NMR(CDCl3): 3.38(s,3H), 3.38(s,3H), 3.58(m,4H), 3.86(m,4H), 5.38(s,4H), 7.18(d,J=8.8 Hz,2H), 7.28(dd,J=9.1,2.2 Hz,1H), 7.67(d,J=2.2 Hz,1H), 8.10(d,J=9.1 Hz,1H), 8.59(d,J=8.8 Hz,2H) IR(KBr) cm-1 : 2877, 1598, 1488, 1214, 1117, 987 MS m/z: 447(M+), 89, 59 Elementary analysis (C22H25NO7S): Calculated (C=59.05,H=5.63,N=3.13); Found (C=59.15,H=5.58,N=2.93)

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter being concentrated
  5. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cce432e77f514bfaba7b4c375bd3f3d9
Source dataset
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05900426

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes