Hydrochloric Acid → HCID 23620793, compound

HRID 1973395Notes

Reaction equation

HRID 1973395 reaction equation
S(Cl)(Cl)(=O)=O.[SH:6][C:7]1[S:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.Cl.[CH3:17][C:18]1([CH3:32])[O:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[O:27][C:28]([NH:30][CH3:31])=[O:29])[CH2:19]1>C1C=CC=CC=1.N1C=CC=CC=1.O>[S:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[C:7]1[S:6][N:30]([CH3:31])[C:28](=[O:29])[O:27][C:24]1[C:25]2[O:26][C:18]([CH3:17])([CH3:32])[CH2:19][C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2566CarbofuranHCID 24648Sulfuryl chlorideHCID 178418395HCID 178418395, compound

Product 1

HCID 23620793HCID 23620793, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 6.75 of sulfuryl chloride in 20 ml of benzene was added dropwise, with vigorous stirring under nitrogen, to a solution of 8.4 g of 2-mercaptobenzothiazole in 150 ml of benzene. The mixture was heated slowly to reflux and maintained under gentle reflux until evolution of hydrogen chloride had ceased. A solution of 11 g of carbofuran in 150 ml of pyridine was added dropwise and the mixture stirred for two hours at reflux under nitrogen. The mixture was poured into water. The organic phase was separated, washed with dilute hydrochloric acid, water and saturated aqueous sodium chloride, then dried. The dry solution was concentrated under reduced pressure and the residue recrystallized from ethanol to give 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (2-benzothiazolylthio)(methyl)carbamate, m.p. 92°-3°. Recrystallization from hexane-benzene increased the melting point to 97°. The n.m.r. spectrum was consistent with the assigned structure.

Workup

  1. temperatureThe mixture was heated slowly
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux under nitrogen
  5. customThe organic phase was separated
  6. washwashed with dilute hydrochloric acid, water and saturated aqueous sodium chloride
  7. customdried
  8. concentrationThe dry solution was concentrated under reduced pressure
  9. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-b476c032e13646e9baed4059f1012cdf
Source dataset
uspto-grants-1976_12
Patent number
US03997549

Reaction notes

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