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Hydrochloric Acid → 3-(3,4-Dimethoxyphenyl)-2-(o-fluorophenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

HRID 67238
Notes
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Reaction equation

HRID 67238 reaction equation
C(=O)C1C=CC(OC)=C(OC)C=1.FC1C=CC=CC=1C=O.[C-]#N.[K+].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:35]([CH:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])O)=[O:36])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.[NH:62]1[CH2:68][CH2:67][CH2:66][CH2:65][NH:64][C:63]1=[S:69].[ClH:70]>CC(C)=O.C(O)C>[ClH:70].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:35]2([OH:36])[N:64]3[CH2:65][CH2:66][CH2:67][CH2:68][N:62]=[C:63]3[S:69][CH:37]2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8400BenzoinHCID 8419VeratraldehydeHCID 9032Potassium CyanideHCID 67970o-FluorobenzaldehydeHCID 7365891,3-Diazepane-2-thioneHCID 205283103,4-Dimethoxy-2'-fluorobenzoin

Product 1

HCID 205283253-(3,4-Dimethoxyphenyl)-2-(o-fluorophenyl)-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 16.6 g. of veratraldehyde, 12.5 g. of o-fluorobenzaldehyde, 8 g. of potassium cyanide, and 100 ml of 65% ethanol is reacted as described in Example 20, yielding 12.5 g. of 3,4-dimethoxy-2'-fluorobenzoin, m.p. 126°-128° C. A 5.8 g. portion of the benzoin derivative is converted to its methanesulfonate ester by the procedure of Example 20, giving 6.7 g. of the ester melting at 111°-113° C. 2.58 g. of the methanesulfonate ester, 0.91 g. of hexahydro-2H-1,3-diazepin-2-thione, and 55 ml. of acetone are mixed and left at room temperature for three days. 7 ml. of 2 N ethanolic hydrogen chloride are added, yielding 2.2 g. of the title compound, melting at 192°-194° C.

Workup

  1. customyielding 12.5 g
  2. customgiving 6.7 g
  3. customyielding 2.2 g

Sources & evidence

ORD record
ord-2c17cee5591046558cc1b46ca1a3b269
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