Benzoin → 2,3,5,6,7,8-Hexahydro-2,3-diphenylthiazolo[3,2-a][1,3]-diazepin-3-ol methanesulfonate

HRID 67234

Reaction equation

HRID 67234 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([C:12]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)O)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:22]1[CH2:28][CH2:27][CH2:26][CH2:25][NH:24][C:23]1=[S:29]>CC(C)=O.O.C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:1][S:2]([O:13][C:12]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][N:22]=[C:23]2[S:29][CH:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:4])=[O:3]

Participants

8

Reactant 3

HCID 8400BenzoinHCID 31297Methanesulfonyl chlorideHCID 7365891,3-Diazepane-2-thione

Product 1

HCID 205283272,3,5,6,7,8-Hexahydro-2,3-diphenylthiazolo[3,2-a][1,3]-diazepin-3-ol methanesulfonate

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 7.75 ml. of methanesulfonyl chloride in 200 ml. of toluene is added, over a period of one hour, to a stirred mixture of 21.2 g. of benzoin, 28 ml. of triethylamine and 100 ml. of toluene. The mixture is allowed to stand 2 hours, 100 ml. of water is added and the emulsion is filtered giving a solid which is washed with water and dried, giving 14.5 g. of benzoin methanesulfonate esters. A 2.90 g. portion of benzoin methanesulfonate esters and 1.30 g. of hexahydro-2H-1,3-diazepin-2-thione are suspended in 50 ml. of warm acetone and heated at reflux for 4 hours. The mixture is cooled, the solid is collected, washed with acetone then ether and dried in vacuo at 60° C., giving 3.9 g. of the desired product, m.p. 176°-178° C.

Workup

  1. additionA mixture of 7.75 ml
  2. filtrationthe emulsion is filtered
  3. customgiving a solid which
  4. washis washed with water
  5. customdried
  6. customgiving 14.5 g
  7. temperatureat reflux for 4 hours
  8. temperatureThe mixture is cooled
  9. customthe solid is collected
  10. washwashed with acetone
  11. dry with materialether and dried in vacuo at 60° C.
  12. customgiving 3.9 g

Sources & evidence

ORD record
ord-064dd7e498d847d686b26da8e63546ce
Source dataset
uspto-grants-1982_08
Patent number
US04344954

Linked notes

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