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Diethyl Ether → Cyclohexylsulfamate

HRID 259608
Notes
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Reaction equation

HRID 259608 reaction equation
[C:1]([NH:4][C:5]([C:18]([O:20][CH3:21])=[O:19])=[CH:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]2[O:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[CH:22]([NH2:25])([CH3:24])[CH3:23].[CH:26]1([NH:32][S:33](=[O:36])(=[O:35])[OH:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.CCOCC>O1CCCC1.CC(C)=O>[CH:26]1([NH:32][S:33](=[O:34])(=[O:35])[O-:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1.[C:1]([NH:4][C:5]([C:18]([O:20][CH3:21])=[O:19])=[CH:6][C:7]1[CH:17]=[CH:16][C:10]([O:11][CH2:12][CH:13]([OH:15])[CH2:14][NH:25][CH:22]([CH3:24])[CH3:23])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6363IsopropylamineHCID 7533CyclamateHCID 541358871-[p-(2-Acetylamino-2-carbomethoxyvinyl)-phenoxy]-2,3-epoxy-propane

Product 2

HCID 3372845CyclohexylsulfamateHCID 538437431-[p-(2-Acetylamino-2-carbomethoxy-vinyl)-phenoxy]-2-hydroxy-3-isoproylamino-propane

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

15.6 g (0.05 mol) of 1-[p-(2-acetylamino-2-carbomethoxyvinyl)-phenoxy]-2,3-epoxy-propane are dissolved in 50 ml of absolute tetrahydrofurane, 4.25 ml (0.05 mol) of isopropylamine are added and thereafter the mixture is heated for 18 hours to the boil under a reflux condenser. It is then evaporated in vacuo and the resulting crude base is dissolved in ethyl acetate. The solution is extracted three times with 20 ml of 1 N hydrochloric acid at a time. The hydrochloric acid extracts are brought to pH 8 with sodium carbonate solution and the crude base which hereupon has separated out is extracted with ethyl acetate. The extract is washed with water, dried over sodium sulphate and evaporated in vacuo. 17 g of crude base are obtained as a brownish oil. This is dissolved in 20 ml of acetone and mixed with a solution of 9 g of N-cyclohexylsulphamic acid in 70 ml of acetone. After addition of ether, the N-cyclohexylsulphamate of 1-[p-(2-acetylamino-2-carbomethoxy-vinyl)-phenoxy]-2-hydroxy-3-isoproylamino-propane, melting point 121°-125° C., is obtained.

Workup

  1. temperaturethe mixture is heated for 18 hours to the boil under a reflux condenser
  2. customIt is then evaporated in vacuo
  3. dissolutionthe resulting crude base is dissolved in ethyl acetate
  4. extractionThe solution is extracted three times with 20 ml of 1 N hydrochloric acid at a time
  5. customthe crude base which hereupon has separated out
  6. extractionis extracted with ethyl acetate
  7. washThe extract is washed with water
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo
  10. custom17 g of crude base are obtained as a brownish oil

Sources & evidence

ORD record
ord-fce01d4b84044b2eaf0fde226456997e
Source dataset
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04038414

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes