2-(Dimethylamino)ethanol → beta-Dimethylaminoethyl-10,11-Dihydro-11-oxodibenzo[b,f]thiepin-3-carboxylate

HRID 485460Notes

Reaction equation

HRID 485460 reaction equation
Cl[C:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:13](=[O:14])[CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[S:9][C:8]=2[CH:19]=1)=[O:3].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24]>O1CCCC1>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][O:24][C:2]([C:4]1[CH:5]=[CH:6][C:7]2[C:13](=[O:14])[CH2:12][C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[S:9][C:8]=2[CH:19]=1)=[O:3]

Participants

4

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 202702113-Chlorocarbonyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Product 1

HCID 70491159beta-Dimethylaminoethyl-10,11-Dihydro-11-oxodibenzo[b,f]thiepin-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1.0 gm. of 3-chlorocarbonyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin as prepared in Example 31, Step 1, in 10 cc. of anhydrous tetrahydrofuran with stirring and add 2 ml. of N,N-dimethylethanolamine. Stir at room temperature for 18 hours and strip the mixture to dryness. Partition the residue between ether and dilute hydrochloric acid and separate the aqueous layer. Basify the aqueous layer with aqueous ammonia and extract with ethyl acetate. Evaporate the organic phase and chromatograph the residue over silica-gel eluting with 90% chloroform in methanol to obtain the title product.

Workup

  1. dissolutionDissolve 1.0 gm
  2. additionadd 2 ml
  3. customPartition the residue between ether and dilute hydrochloric acid
  4. customseparate the aqueous layer
  5. extractionBasify the aqueous layer with aqueous ammonia and extract with ethyl acetate
  6. customEvaporate the organic phase and chromatograph the residue over silica-gel
  7. washeluting with 90% chloroform in methanol

Sources & evidence

ORD record
ord-d82a00c251d24bc4bbf8cb4cdb09fcfe
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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