Trifluoroacetic acid → HCID 13338630, compound

HRID 2417921Notes

Reaction equation

HRID 2417921 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3](O)=O.[N:8]1[CH2:9][CH2:10][CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:15]=3[S:14][C:13]=12.[BH4-].[Na+].[OH-].[NH4+]>>[F:1][C:2]([F:7])([F:6])[CH2:3][NH:21][C:18]1[CH:19]=[CH:20][C:15]2[S:14][C:13]3=[N:8][CH2:9][CH2:10][CH2:11][N:12]3[C:16]=2[CH:17]=1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 133385843,4-Dihydro-2H-pyrimido[2,1-b][1,3]benzothiazol-7-amine

Product 1

HCID 13338630HCID 13338630, compound

Procedure

To a stirred mixture of 45 parts of trifluoroacetic acid and 2 parts of 3,4-dihydro-2H-pyrimido[2,1-b]benzothiazol-7-amine are added portionwise, during a 4 hours-period, 3 parts of sodium borohydride at 30°-40° C. while nitrogen gas is introduced. The reaction mixture is poured onto ice-water and the whole is alkalized with ammonium hydroxide. The product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 8 parts of acetonitrile, yielding 0.55 parts of 3,4-dihydro-N-(2,2,2-trifluoroethyl)-2H-pyrimido[2,1-b]benzothiazol-7-amine; mp. 186.7° C.

Workup

  1. additionis introduced
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionThe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 8 parts of acetonitrile

Sources & evidence

ORD record
ord-c6b05e3ae7d747aeacc482637d0df0c2
Source dataset
uspto-grants-1984_09
Patent number
US04471117

Reaction notes

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