Triethylamine → 2-(o-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol

HRID 67228

Reaction equation

HRID 67228 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH:4](O)[C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[NH:34]1[CH2:40][CH2:39][CH2:38][CH2:37][NH:36][C:35]1=[S:41]>CC(C)=O.C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH:4]1[S:41][C:35]2=[N:34][CH2:40][CH2:39][CH2:38][CH2:37][N:36]2[C:5]1([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)[OH:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 7365891,3-Diazepane-2-thioneHCID 150442192-(2-Chlorophenyl)-1-(3,4-dimethoxyphenyl)-2-hydroxyethan-1-one

Product 1

HCID 130682872-(o-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

A 6.13 g. portion of 2'-chloro-3,4-dimethoxybenzoin, 5.6 ml. of triethylamine and 20 ml. of toluene are mixed and stirred. A mixture of 1.55 ml. of methanesulfonyl chloride in 40 ml. of toluene is added over a period of one hour. A 50 ml. portion of water and more toluene are added. The organic layer is separated, washed with water and concentrated in vacuo to give 8.3 g. of 2'-chloro-3,4-dimethoxybenzoin methanesulfonate ester as a viscous oil. A mixture of this oil in 30 ml. of acetone is added to a stirred mixture of 1.95 g. of hexahydro-2H-1,3-diazepine-2-Thione in 150 ml. of acetone. The resulting mixture is stirred for 3 hours, then 3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether is added producing a gum. The mixture is concentrated free of solvents, 100 ml. of water and 2 ml. of ammonium hydroxide are added and the solid is filtered and washed with water. This solid is dissolved in 20 ml. of ethanol and refrigerated giving 1.3 g. of the desired product, m.p. 98°-100° C.

Workup

  1. additionA mixture of 1.55 ml
  2. customThe organic layer is separated
  3. washwashed with water
  4. concentrationconcentrated in vacuo
  5. customto give 8.3 g
  6. additionA mixture of this oil in 30 ml
  7. stirringThe resulting mixture is stirred for 3 hours
  8. concentration3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether
  9. additionis added
  10. customproducing a gum
  11. concentrationThe mixture is concentrated free of solvents, 100 ml
  12. additionof ammonium hydroxide are added
  13. filtrationthe solid is filtered
  14. washwashed with water
  15. dissolutionThis solid is dissolved in 20 ml
  16. customof ethanol and refrigerated giving 1.3 g

Sources & evidence

ORD record
ord-3dd7ab568a7044628a6fc2869f0d7c63
Source dataset
uspto-grants-1982_08
Patent number
US04344954

Linked notes

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