Ammonia → HCID 21162386, compound

HRID 894090Notes

Reaction equation

HRID 894090 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1)=[O:13].ClS(O)(=O)=O.N.[OH-].[Na+].[CH:35]1([N:41]=[C:42]=[O:43])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CC(C)=O.O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:12]([NH:14][CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([S:23]([NH:26][C:42]([NH:41][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:43])(=[O:24])=[O:25])=[CH:21][CH:22]=1)=[O:13]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 18502Cyclohexyl isocyanateHCID 24638Chlorosulfonic acid2×HCID 21162326HCID 21162326, compound

Product 1

HCID 21162386HCID 21162386, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

5.5 g of 4-(2-[1-oxo-1,2,3,4-tetrahydroisoquinoline-2-carboxamido]-ethyl)-benzenesulfonamide (melting point 197°-198° C., prepared from 1-oxo-1,2,3,4-tetrahydroisoquinoline-2-(N-2-phenylethyl)-carboxamide [melting point 98°-99° C., prepared from 1-oxo-1,2,3,4-tetrahydro-isoquinoline and 2-phenylethyl isocyanate] and chlorosulfonic acid, with subsequent reaction of the sulfochloride with ammonia) are suspended in 75 ml of acetone and 7.5 ml of 2 N sodium hydroxide solution and the mixture is cooled to 0°-5° C. 2.15 g of cyclohexyl isocyanate in 10 ml of acetone are added dropwise, whilst stirring, and the mixture is then stirred for one hour whilst cooling with ice and for three hours at room temperature. The precipitate is dissolved by adding water. After removing the acetone in vacuo, the aqueous solution which remains is acidified with dilute hydrochloric acid. The N-(4-[2-(1-oxo-1,2,3,4-tetrahydro-isoquinoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-urea which has precipitated is filtered off with suction, reprecipitated once from dilute ammonia solution by means of dilute hydrochloride acid, filtered off with suction, dried and recrystallized from ethanol. The product thus obtained melts at 197°-199° C.

Workup

  1. stirringthe mixture is then stirred for one hour
  2. dissolutionThe precipitate is dissolved
  3. customAfter removing the acetone in vacuo
  4. customThe N-(4-[2-(1-oxo-1,2,3,4-tetrahydro-isoquinoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl-urea which has precipitated
  5. filtrationis filtered off with suction
  6. customreprecipitated once from dilute ammonia solution by means of dilute hydrochloride acid
  7. filtrationfiltered off with suction
  8. customdried
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8d0030d6efcf4bfa829225f21bb5db20
Source dataset
uspto-grants-1981_08
Patent number
US04282239

Reaction notes

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