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Hydrochloric Acid → 2-(p-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

HRID 67239
Notes
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Reaction equation

HRID 67239 reaction equation
C1C(C=O)=CC2OCOC=2C=1.FC1C=CC(C=O)=CC=1.[C-]#N.[K+].[F:24][C:25]1[CH:43]=[CH:42][C:28]([CH:29](O)[C:30](=[O:40])[C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)=[CH:27][CH:26]=1.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[NH:60]1[CH2:66][CH2:65][CH2:64][CH2:63][NH:62][C:61]1=[S:67].[ClH:68]>CC(C)=O.C(O)C>[ClH:68].[F:24][C:25]1[CH:43]=[CH:42][C:28]([CH:29]2[S:67][C:61]3=[N:60][CH2:66][CH2:65][CH2:64][CH2:63][N:62]3[C:30]2([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[OH:40])=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8400BenzoinHCID 8438PiperonalHCID 9032Potassium CyanideHCID 680234-FluorobenzaldehydeHCID 7365891,3-Diazepane-2-thioneHCID 542048934'-Fluoro-3,4-methylenedioxybenzoin

Product 1

HCID 205283162-(p-Fluorophenyl)-3-(3,4-methylenedioxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

A mixture consisting of 12 g. of piperonal 8.4 ml. of p-fluorobenzaldehyde, 6 g. of potassium cyanide, and 80 ml. of 65% ethanol is reacted as described in Example 20, giving 11.7 g. of 4'-fluoro-3,4-methylenedioxybenzoin as an uncrystallizable oil. 9.0 g. of this benzoin is converted to its methanesulfonate ester by the procedure of Example 20, yielding 9.8 g. of ester as an uncrystallizable oil. The reaction of 4.9 g. of the crude methanesulfonate ester, and 1.16 g. of hexahydro-2H-1,3-diazepin-2-thione in 80 ml. of acetone, followed by treatment with 5 ml of 2 N ethanolic hydrogen chloride gives the title compound melting at 211°-213° C.

Workup

  1. customgiving 11.7 g
  2. customyielding 9.8 g
  3. customThe reaction of 4.9 g

Sources & evidence

ORD record
ord-ba8adce569ad490c9586f19986e695ad
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04344954

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes