Dicyclohexylcarbodiimide → HCID 86741818, compound

HRID 2309670Notes

Reaction equation

HRID 2309670 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[CH:25]([CH2:29][C:30]([OH:32])=[O:31])[C:26](O)=[S:27]>C(COC)OC>[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[CH:25]1[CH2:29][C:30](=[O:31])[O:32][C:26]1=[S:27]

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 178525532HCID 178525532, compound

Product 1

HCID 86741818HCID 86741818, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 6.18 parts of dicyclohexylcarbodiimide in 30 parts by volume of dimethoxyethane is added dropwise, over 1.5 hours, to a stirred solution of 8.49 parts of benzothiazol-2-ylthio succinic acid prepared as in Example 1A in dimethoxyethane (70 parts by volume). The reaction is exothermic and the temperature is maintained at 25°-27° with cooling. When the addition is complete, stirring is continued for a further 1.5 hours and the precipitated dicyclohexylurea is removed by filtration. The filtrate is evaporated in vacuo and the residual solid is recrystallised from a mixture of dichloromethane and cyclohexane to give benzothiazol-2-ylthio succinic anhydride m.p. 129°-129° (with decomposition).

Workup

  1. temperaturethe temperature is maintained at 25°-27°
  2. temperaturewith cooling
  3. additionWhen the addition
  4. customthe precipitated dicyclohexylurea is removed by filtration
  5. customThe filtrate is evaporated in vacuo
  6. customthe residual solid is recrystallised from a mixture of dichloromethane and cyclohexane

Sources & evidence

ORD record
ord-da25f27ad3fa434abba9e6bf5f683b58
Source dataset
uspto-grants-1987_09
Patent number
US04696763

Reaction notes

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