N-(2-hydroxy-1,1-dimethylethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea → 4,5-dihydro-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4,4-dimethyl-2-thiazolamine

HRID 2106752Notes

Reaction equation

HRID 2106752 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[S:8])([CH3:5])[CH3:4]>C(O)=O>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:13]3[CH:14]=[CH:15][C:10]([NH:9][C:7]4[S:8][CH2:2][C:3]([CH3:4])([CH3:5])[N:6]=4)=[CH:11][CH:12]=3)[CH2:17][CH2:18]2)=[CH:23][CH:24]=1

Participants

3

Reactant 1

HCID 15125467N-(2-hydroxy-1,1-dimethylethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea

Product 1

HCID 151254684,5-dihydro-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4,4-dimethyl-2-thiazolamineYield 62.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 74 parts of N-(2-hydroxy-1,1-dimethylethyl)-N'-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]thiourea and 360 parts of formic acid was stirred for 4 hours at 70° C. The reaction mixture was evaporated and the residue was dissolved in 260 parts of dichloromethane. The whole was neutralized with a sodium hydrogen carbonate solution. The precipitated product was filtered off, washed with water and dichloromethane and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off and dried, yielding 44.1 parts (62.4%) of 4,5-dihydro-N-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4,4-dimethyl-2-thiazolamine; mp. 232.0° C. (int. 8).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in 260 parts of dichloromethane
  3. filtrationThe precipitated product was filtered off
  4. washwashed with water and dichloromethane
  5. custompurified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from 4-methyl-2-pentanone
  10. filtrationThe product was filtered off
  11. customdried

Sources & evidence

ORD record
ord-9ba1e40c299a4656a0099ceb1262a3d4
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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